CA1024526A - Process for preparing novel benzyloxysulfamides and the salts thereof - Google Patents
Process for preparing novel benzyloxysulfamides and the salts thereofInfo
- Publication number
- CA1024526A CA1024526A CA204,630A CA204630A CA1024526A CA 1024526 A CA1024526 A CA 1024526A CA 204630 A CA204630 A CA 204630A CA 1024526 A CA1024526 A CA 1024526A
- Authority
- CA
- Canada
- Prior art keywords
- avec
- formule
- que
- produit
- fait
- 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.)
- Expired
Links
- OVLROWNKNHOVLL-UHFFFAOYSA-N (sulfamoylamino)oxymethylbenzene Chemical class NS(=O)(=O)NOCC1=CC=CC=C1 OVLROWNKNHOVLL-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 title 1
- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 7
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- QJOYZDNNXZTPIW-UHFFFAOYSA-N 1-chloro-2-[(sulfamoylamino)oxymethyl]benzene Chemical compound ClC1=C(CONS(=O)(=O)N)C=CC=C1 QJOYZDNNXZTPIW-UHFFFAOYSA-N 0.000 claims description 3
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 claims description 3
- WJWMBNQCKBRAHA-UHFFFAOYSA-N o-[(2-chlorophenyl)methyl]hydroxylamine Chemical compound NOCC1=CC=CC=C1Cl WJWMBNQCKBRAHA-UHFFFAOYSA-N 0.000 claims description 2
- DRIQCKQSXPOKGN-UHFFFAOYSA-N 1-fluoro-2-[(sulfamoylamino)oxymethyl]benzene Chemical compound FC1=C(CONS(=O)(=O)N)C=CC=C1 DRIQCKQSXPOKGN-UHFFFAOYSA-N 0.000 claims 3
- OUHKQMQWIDUZDW-UHFFFAOYSA-N o-[(2-fluorophenyl)methyl]hydroxylamine Chemical compound NOCC1=CC=CC=C1F OUHKQMQWIDUZDW-UHFFFAOYSA-N 0.000 claims 2
- 229940125681 anticonvulsant agent Drugs 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- 239000002249 anxiolytic agent Substances 0.000 abstract 1
- 230000000949 anxiolytic effect Effects 0.000 abstract 1
- 229940005530 anxiolytics Drugs 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 26
- 150000001408 amides Chemical class 0.000 description 20
- 241001465754 Metazoa Species 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 238000013019 agitation Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 241000699729 Muridae Species 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BUSVXLMCEYFMCS-UHFFFAOYSA-N 2-(6-bromopyridin-2-yl)ethanol Chemical compound OCCC1=CC=CC(Br)=N1 BUSVXLMCEYFMCS-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 101100407060 Caenorhabditis elegans par-6 gene Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 241000206607 Porphyra umbilicalis Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- NMYFFUUIFUDPRN-UHFFFAOYSA-N o-[(3-chlorophenyl)methyl]hydroxylamine Chemical compound NOCC1=CC=CC(Cl)=C1 NMYFFUUIFUDPRN-UHFFFAOYSA-N 0.000 description 1
- INUFRNDIHFACLU-UHFFFAOYSA-N o-[(3-fluorophenyl)methyl]hydroxylamine Chemical compound NOCC1=CC=CC(F)=C1 INUFRNDIHFACLU-UHFFFAOYSA-N 0.000 description 1
- YTBXSBIQXOHSRA-UHFFFAOYSA-N o-[(4-bromophenyl)methyl]hydroxylamine Chemical compound NOCC1=CC=C(Br)C=C1 YTBXSBIQXOHSRA-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7325759A FR2244483B1 (xx) | 1973-07-13 | 1973-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1024526A true CA1024526A (en) | 1978-01-17 |
Family
ID=9122547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA204,630A Expired CA1024526A (en) | 1973-07-13 | 1974-07-12 | Process for preparing novel benzyloxysulfamides and the salts thereof |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3904586A (xx) |
| JP (1) | JPS5037750A (xx) |
| BE (1) | BE817557A (xx) |
| CA (1) | CA1024526A (xx) |
| CH (1) | CH584193A5 (xx) |
| DE (1) | DE2433681A1 (xx) |
| DK (1) | DK137272B (xx) |
| FR (1) | FR2244483B1 (xx) |
| GB (1) | GB1429914A (xx) |
| IE (1) | IE39721B1 (xx) |
| LU (1) | LU70515A1 (xx) |
| NL (1) | NL7409446A (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK595489D0 (da) * | 1989-11-27 | 1989-11-27 | Neurosearch As | Hydroxycarbonylderivater og fremgangsmaade til fremstilling af samme |
| US5225604A (en) * | 1989-11-27 | 1993-07-06 | Neurosearch A/S | Hydroxycarbonyl derivatives and process for making the same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH452504A (de) * | 1962-11-20 | 1968-03-15 | Ciba Geigy | Neues Sulfamid |
| GB1268399A (en) * | 1968-07-05 | 1972-03-29 | Soc Ind Fab Antibiotiques Sifa | New amides of sulfamic acid, their alkali metal salts and process for preparation thereof |
-
1973
- 1973-07-13 FR FR7325759A patent/FR2244483B1/fr not_active Expired
-
1974
- 1974-07-10 US US487036A patent/US3904586A/en not_active Expired - Lifetime
- 1974-07-11 BE BE146481A patent/BE817557A/xx unknown
- 1974-07-11 LU LU70515A patent/LU70515A1/xx unknown
- 1974-07-12 CH CH967974A patent/CH584193A5/xx not_active IP Right Cessation
- 1974-07-12 DE DE2433681A patent/DE2433681A1/de active Pending
- 1974-07-12 NL NL7409446A patent/NL7409446A/xx not_active Application Discontinuation
- 1974-07-12 DK DK375474AA patent/DK137272B/da unknown
- 1974-07-12 CA CA204,630A patent/CA1024526A/en not_active Expired
- 1974-07-12 JP JP49079293A patent/JPS5037750A/ja active Pending
- 1974-07-15 IE IE1495/74A patent/IE39721B1/xx unknown
- 1974-07-15 GB GB3119374A patent/GB1429914A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE39721B1 (en) | 1978-12-20 |
| US3904586A (en) | 1975-09-09 |
| FR2244483B1 (xx) | 1977-07-01 |
| CH584193A5 (xx) | 1977-01-31 |
| LU70515A1 (xx) | 1975-03-27 |
| GB1429914A (en) | 1976-03-31 |
| NL7409446A (nl) | 1975-01-15 |
| FR2244483A1 (xx) | 1975-04-18 |
| DK375474A (xx) | 1975-03-03 |
| DK137272B (da) | 1978-02-13 |
| DK137272C (xx) | 1978-07-17 |
| IE39721L (en) | 1975-01-13 |
| DE2433681A1 (de) | 1975-01-30 |
| JPS5037750A (xx) | 1975-04-08 |
| BE817557A (fr) | 1975-01-13 |
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