NO136460B - - Google Patents
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- Publication number
- NO136460B NO136460B NO4949/71A NO494971A NO136460B NO 136460 B NO136460 B NO 136460B NO 4949/71 A NO4949/71 A NO 4949/71A NO 494971 A NO494971 A NO 494971A NO 136460 B NO136460 B NO 136460B
- Authority
- NO
- Norway
- Prior art keywords
- formula
- benzamide
- methoxy
- sulfamoyl
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 13
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 6
- SQAILWDRVDGLGY-UHFFFAOYSA-N 2-methoxy-5-sulfamoylbenzoic acid Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(O)=O SQAILWDRVDGLGY-UHFFFAOYSA-N 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 230000009435 amidation Effects 0.000 description 3
- 238000007112 amidation reaction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1226771A CH547797A (de) | 1971-08-20 | 1971-08-20 | Verfahren zur herstellung von n - ((1-aethyl-pyrrolidinyl2)-methyl) -2-methoxy-5-sulfamoyl-benzamid. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO136460B true NO136460B (he) | 1977-05-31 |
| NO136460C NO136460C (no) | 1977-09-07 |
Family
ID=4381427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4949/71A NO136460C (no) | 1971-08-20 | 1971-12-30 | Fremgangsm}te ved fremstilling av n-((1-ethylpyrrolidinyl-2)-methyl)-2-methoxy-5-sulfamoyl-benzamid. |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS4829764A (he) |
| KR (1) | KR780000067B1 (he) |
| AT (1) | AT311328B (he) |
| BE (1) | BE774104A (he) |
| CA (1) | CA928714A (he) |
| CH (1) | CH547797A (he) |
| CS (1) | CS177818B2 (he) |
| DE (1) | DE2152370A1 (he) |
| DK (1) | DK126325B (he) |
| ES (1) | ES396718A1 (he) |
| FR (1) | FR2111372A5 (he) |
| GB (1) | GB1328747A (he) |
| HU (1) | HU166567B (he) |
| IE (1) | IE35821B1 (he) |
| IL (1) | IL38098A (he) |
| LU (1) | LU64275A1 (he) |
| MC (1) | MC897A1 (he) |
| NL (1) | NL7114902A (he) |
| NO (1) | NO136460C (he) |
| OA (1) | OA03928A (he) |
| PL (1) | PL84446B1 (he) |
| RO (1) | RO62479A (he) |
| SE (1) | SE376914B (he) |
| YU (1) | YU34286B (he) |
| ZA (1) | ZA717543B (he) |
| ZM (1) | ZM17771A1 (he) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK154137B (da) * | 1977-01-27 | 1988-10-17 | Shionogi & Co | Analogifremgangsmaade til fremstilling af meta-sulfonamido-benzamidderivater |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2252336B1 (he) * | 1973-11-27 | 1977-03-04 | Ile De France | |
| JPS5170235A (he) * | 1974-12-16 | 1976-06-17 | Toyo Aluminium Kk | |
| WO1991017144A1 (en) * | 1990-05-02 | 1991-11-14 | Yoshitomi Pharmaceutical Industries, Ltd. | Amide compound, pharmaceutical use thereof and novel 1-substituted pyrrolidinemethyl-amines |
-
1971
- 1971-08-20 CH CH1226771A patent/CH547797A/xx not_active IP Right Cessation
- 1971-10-14 FR FR7136941A patent/FR2111372A5/fr not_active Expired
- 1971-10-18 BE BE774104A patent/BE774104A/xx not_active IP Right Cessation
- 1971-10-21 DE DE19712152370 patent/DE2152370A1/de active Pending
- 1971-10-28 NL NL7114902A patent/NL7114902A/xx unknown
- 1971-11-05 ES ES396718A patent/ES396718A1/es not_active Expired
- 1971-11-08 CA CA127136A patent/CA928714A/en not_active Expired
- 1971-11-08 IL IL38098A patent/IL38098A/he unknown
- 1971-11-09 YU YU2821/71A patent/YU34286B/xx unknown
- 1971-11-09 SE SE7114275A patent/SE376914B/xx unknown
- 1971-11-09 ZA ZA717543A patent/ZA717543B/xx unknown
- 1971-11-09 MC MC956A patent/MC897A1/xx unknown
- 1971-11-16 LU LU64275D patent/LU64275A1/xx unknown
- 1971-11-18 IE IE1459/71A patent/IE35821B1/xx unknown
- 1971-11-29 DK DK584371AA patent/DK126325B/da not_active IP Right Cessation
- 1971-12-01 HU HUFA900A patent/HU166567B/hu unknown
- 1971-12-01 ZM ZM177/71*7A patent/ZM17771A1/xx unknown
- 1971-12-06 KR KR7101750A patent/KR780000067B1/ko active
- 1971-12-06 GB GB5649571A patent/GB1328747A/en not_active Expired
- 1971-12-07 OA OA54434A patent/OA03928A/xx unknown
- 1971-12-08 PL PL1971152013A patent/PL84446B1/pl unknown
- 1971-12-10 AT AT1064371A patent/AT311328B/de not_active IP Right Cessation
- 1971-12-29 CS CS9068A patent/CS177818B2/cs unknown
- 1971-12-29 JP JP47004153A patent/JPS4829764A/ja active Pending
- 1971-12-30 NO NO4949/71A patent/NO136460C/no unknown
-
1972
- 1972-01-15 RO RO7200069412A patent/RO62479A/ro unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK154137B (da) * | 1977-01-27 | 1988-10-17 | Shionogi & Co | Analogifremgangsmaade til fremstilling af meta-sulfonamido-benzamidderivater |
Also Published As
| Publication number | Publication date |
|---|---|
| RO62479A (fr) | 1978-02-15 |
| IE35821B1 (en) | 1976-05-26 |
| DE2152370A1 (de) | 1973-02-22 |
| IE35821L (en) | 1973-02-20 |
| YU282171A (en) | 1978-10-31 |
| HU166567B (he) | 1975-04-28 |
| ES396718A1 (es) | 1974-05-16 |
| CS177818B2 (he) | 1977-08-31 |
| MC897A1 (fr) | 1972-06-22 |
| PL84446B1 (he) | 1976-04-30 |
| LU64275A1 (he) | 1972-06-02 |
| BE774104A (fr) | 1972-04-18 |
| JPS4829764A (he) | 1973-04-19 |
| DK126325B (da) | 1973-07-02 |
| KR780000067B1 (en) | 1978-03-30 |
| NL7114902A (he) | 1973-02-22 |
| CH547797A (de) | 1974-04-11 |
| IL38098A (he) | 1974-12-31 |
| AU3572171A (en) | 1973-05-24 |
| OA03928A (fr) | 1975-08-14 |
| ZA717543B (en) | 1972-08-30 |
| SE376914B (he) | 1975-06-16 |
| AT311328B (de) | 1973-11-12 |
| YU34286B (en) | 1979-04-30 |
| ZM17771A1 (he) | 1972-08-21 |
| IL38098A0 (en) | 1972-01-27 |
| GB1328747A (en) | 1973-08-30 |
| CA928714A (en) | 1973-06-19 |
| FR2111372A5 (he) | 1972-06-02 |
| NO136460C (no) | 1977-09-07 |
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