CA2391978A1 - Procede de preparation de sulfamides - Google Patents
Procede de preparation de sulfamides Download PDFInfo
- Publication number
- CA2391978A1 CA2391978A1 CA002391978A CA2391978A CA2391978A1 CA 2391978 A1 CA2391978 A1 CA 2391978A1 CA 002391978 A CA002391978 A CA 002391978A CA 2391978 A CA2391978 A CA 2391978A CA 2391978 A1 CA2391978 A1 CA 2391978A1
- Authority
- CA
- Canada
- Prior art keywords
- optionally substituted
- alkyl
- formula
- phenyl
- aryl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 13
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- -1 aryl sulfamide Chemical compound 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- REBMRHHTBYKLDT-UHFFFAOYSA-N n-(4-methylphenyl)-2-oxo-1,3-oxazolidine-3-sulfonamide Chemical compound C1=CC(C)=CC=C1NS(=O)(=O)N1C(=O)OCC1 REBMRHHTBYKLDT-UHFFFAOYSA-N 0.000 description 5
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 5
- XJEVFFNOMKXBLU-UHFFFAOYSA-N 4-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C=C1 XJEVFFNOMKXBLU-UHFFFAOYSA-N 0.000 description 4
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010908 decantation Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
- LWTSNAAKXGLFDJ-UHFFFAOYSA-N 2-oxo-n-propan-2-yl-1,3-oxazolidine-3-sulfonamide Chemical compound CC(C)NS(=O)(=O)N1CCOC1=O LWTSNAAKXGLFDJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 0 *NS(N(*)*)(=O)=O Chemical compound *NS(N(*)*)(=O)=O 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
- UOCUSOBVEHOMMB-UHFFFAOYSA-N 2h-1$l^{6},2,3-benzothiadiazine 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)NN=CC2=C1 UOCUSOBVEHOMMB-UHFFFAOYSA-N 0.000 description 1
- NMEAGYKSZYLEAS-UHFFFAOYSA-N 4-methylsulfonylaniline;hydrochloride Chemical compound Cl.CS(=O)(=O)C1=CC=C(N)C=C1 NMEAGYKSZYLEAS-UHFFFAOYSA-N 0.000 description 1
- DPTWDHTZECAMSZ-UHFFFAOYSA-N CCN(CC)CC.CC(C=C1)=CC=C1N Chemical compound CCN(CC)CC.CC(C=C1)=CC=C1N DPTWDHTZECAMSZ-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/34—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D263/36—One oxygen atom
- C07D263/38—One oxygen atom attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
L'invention concerne un procédé de production de sulfamide d'aryle représenté par la formule générale (I) dans laquelle R?1¿, R?2¿ et R?3¿ représentent chacun un hydrogène, un alkyle, un cycloalkyle ou un aryle, à condition qu'au moins un des R?1¿, R?2¿ et R¿3? représente un aryle, consistant à faire réagir un composé de la formule générale (II) dans laquelle R?4¿, R?5¿, R?6¿, R?7¿, R?8¿ et R?9¿ représentent chacun un hydrogène, un alkyle ou un aryle et n est égal à 0 ou 1, avec une amine de la formule R?2¿R?3¿NH (III), en présence d'une base forte.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9927302A GB2356398A (en) | 1999-11-18 | 1999-11-18 | Preparation of arylsulfamides |
| GB9927302.1 | 1999-11-18 | ||
| PCT/US2000/028877 WO2001036383A1 (fr) | 1999-11-18 | 2000-11-03 | Procede de preparation de sulfamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2391978A1 true CA2391978A1 (fr) | 2001-05-25 |
Family
ID=10864756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002391978A Abandoned CA2391978A1 (fr) | 1999-11-18 | 2000-11-03 | Procede de preparation de sulfamides |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1235795A1 (fr) |
| JP (1) | JP2003514797A (fr) |
| AU (1) | AU1434301A (fr) |
| CA (1) | CA2391978A1 (fr) |
| GB (1) | GB2356398A (fr) |
| WO (1) | WO2001036383A1 (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002070467A1 (fr) | 2001-02-26 | 2002-09-12 | 4Sc Ag | Derives de diphenyluree, de diamide d'acide diphenyloxalique et de diamide d'acide diphenylsulfurique et leur utilisation comme medicaments |
| MXPA04000224A (es) | 2001-07-10 | 2005-07-25 | 4Sc Ag | Novedosos compuestos como agentes antiinflamatorios, inmunomoduladores y antiproliferativos. |
| GB0423554D0 (en) | 2004-10-22 | 2004-11-24 | Cancer Rec Tech Ltd | Therapeutic compounds |
| EP2013207B1 (fr) | 2006-04-26 | 2012-04-25 | Cancer Research Technology Limited | Composés d'imidazo[4,5-b]pyridin-2-one et leurs analogues en tant que composés de traitement du cancer |
| NZ586418A (en) | 2007-12-19 | 2012-09-28 | Cancer Rec Tech Ltd | Pyrido[2,3-b]pyrazine-8-substituted compounds and their use |
| GB0807609D0 (en) | 2008-04-25 | 2008-06-04 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| CN101569864B (zh) * | 2008-04-29 | 2011-08-03 | 中山大学 | 手性磺胺类有机小分子催化剂及其应用 |
| DK2531502T3 (da) | 2010-02-01 | 2014-05-19 | Cancer Rec Tech Ltd | 1-(5-tert-butyl-2-phenyl-2h-pyrazol-3-yl)-3-[2-fluoro-4-(1-methyl-2-oxo-2,3-dihydro-1h-imidazo[4,5-b]pyridin-7-yloxy)-phenyl]-urea og associerede forbindelser og ders anvendelse i terapi |
| GB201320732D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Methods of chemical synthesis |
| GB201320729D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| CN108250121A (zh) * | 2016-12-28 | 2018-07-06 | 上海长森药业有限公司 | 磺酰胺-芳基酰胺类化合物及其治疗乙型肝炎的药物用途 |
-
1999
- 1999-11-18 GB GB9927302A patent/GB2356398A/en not_active Withdrawn
-
2000
- 2000-11-03 WO PCT/US2000/028877 patent/WO2001036383A1/fr not_active Ceased
- 2000-11-03 EP EP00976591A patent/EP1235795A1/fr not_active Withdrawn
- 2000-11-03 AU AU14343/01A patent/AU1434301A/en not_active Abandoned
- 2000-11-03 CA CA002391978A patent/CA2391978A1/fr not_active Abandoned
- 2000-11-03 JP JP2001538874A patent/JP2003514797A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003514797A (ja) | 2003-04-22 |
| EP1235795A1 (fr) | 2002-09-04 |
| WO2001036383A1 (fr) | 2001-05-25 |
| AU1434301A (en) | 2001-05-30 |
| GB9927302D0 (en) | 2000-01-12 |
| GB2356398A (en) | 2001-05-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |