PL97785B1 - Sposob wytwarzania nowych pochodnych 1-sulfonylobenzimidazolu - Google Patents
Sposob wytwarzania nowych pochodnych 1-sulfonylobenzimidazolu Download PDFInfo
- Publication number
- PL97785B1 PL97785B1 PL1975181664A PL18166475A PL97785B1 PL 97785 B1 PL97785 B1 PL 97785B1 PL 1975181664 A PL1975181664 A PL 1975181664A PL 18166475 A PL18166475 A PL 18166475A PL 97785 B1 PL97785 B1 PL 97785B1
- Authority
- PL
- Poland
- Prior art keywords
- amino
- carboxylic acid
- acid
- benzimidazole
- ester
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 allyloxycarbonyl Chemical group 0.000 claims description 180
- 239000002253 acid Substances 0.000 claims description 178
- COYPLDIXZODDDL-UHFFFAOYSA-N 3h-benzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=CNC2=C1 COYPLDIXZODDDL-UHFFFAOYSA-N 0.000 claims description 82
- 125000004494 ethyl ester group Chemical group 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 39
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- 125000001424 substituent group Chemical group 0.000 claims description 6
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- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical group O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 1
- UFKRTEWFEYWIHD-UHFFFAOYSA-N n-(4-cyanophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C#N)C=C1 UFKRTEWFEYWIHD-UHFFFAOYSA-N 0.000 description 1
- SPAOQNOLRMENDZ-UHFFFAOYSA-N n-[4-(cyanomethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(CC#N)C=C1 SPAOQNOLRMENDZ-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- WCVVIGQKJZLJDB-UHFFFAOYSA-N o-butylhydroxylamine Chemical compound CCCCON WCVVIGQKJZLJDB-UHFFFAOYSA-N 0.000 description 1
- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MTHMVLLKCNMJQL-UHFFFAOYSA-N oxalonitrile hydrobromide Chemical compound Br.N#CC#N MTHMVLLKCNMJQL-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical class NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
- YSPWSQNKRBSICH-UHFFFAOYSA-N thiophene-3-sulfonyl chloride Chemical compound ClS(=O)(=O)C=1C=CSC=1 YSPWSQNKRBSICH-UHFFFAOYSA-N 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/22—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms directly attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48484174A | 1974-07-01 | 1974-07-01 | |
| US57420275A | 1975-05-08 | 1975-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL97785B1 true PL97785B1 (pl) | 1978-03-30 |
Family
ID=27048159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1975181664A PL97785B1 (pl) | 1974-07-01 | 1975-06-30 | Sposob wytwarzania nowych pochodnych 1-sulfonylobenzimidazolu |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS51125078A (is") |
| AR (1) | AR212431A1 (is") |
| AT (1) | AT344158B (is") |
| BG (1) | BG27083A3 (is") |
| CA (1) | CA1026335A (is") |
| CH (1) | CH617428A5 (is") |
| DD (1) | DD121109A5 (is") |
| DE (1) | DE2528846A1 (is") |
| DK (1) | DK140313B (is") |
| ES (1) | ES439049A1 (is") |
| FR (1) | FR2276821A1 (is") |
| GB (1) | GB1511724A (is") |
| HU (1) | HU172941B (is") |
| IE (1) | IE41394B1 (is") |
| IL (1) | IL47587A (is") |
| NL (1) | NL7507840A (is") |
| PH (1) | PH14623A (is") |
| PL (1) | PL97785B1 (is") |
| RO (1) | RO68748A (is") |
| SE (1) | SE415254B (is") |
| SU (1) | SU786892A3 (is") |
| YU (1) | YU164075A (is") |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR66420B (is") * | 1976-12-15 | 1981-03-20 | Lilly Co Eli | |
| GB8504818D0 (en) * | 1985-02-25 | 1985-03-27 | Imperial Chemical Industries Plc | Extraction of metal values |
| JPS625966A (ja) * | 1985-07-03 | 1987-01-12 | Nippon Shinyaku Co Ltd | ベンズイミダゾ−ル誘導体 |
| EP2565178A1 (en) * | 2002-10-03 | 2013-03-06 | Ono Pharmaceutical Co., Ltd. | LPA Receptor Antagonists |
-
1975
- 1975-06-25 JP JP50079313A patent/JPS51125078A/ja active Pending
- 1975-06-26 YU YU01640/75A patent/YU164075A/xx unknown
- 1975-06-27 GB GB27406/75A patent/GB1511724A/en not_active Expired
- 1975-06-27 IL IL47587A patent/IL47587A/xx unknown
- 1975-06-27 DE DE19752528846 patent/DE2528846A1/de not_active Withdrawn
- 1975-06-27 DK DK292175AA patent/DK140313B/da unknown
- 1975-06-27 RO RO7582673A patent/RO68748A/ro unknown
- 1975-06-27 CA CA230,418A patent/CA1026335A/en not_active Expired
- 1975-06-30 IE IE1442/75A patent/IE41394B1/xx unknown
- 1975-06-30 PL PL1975181664A patent/PL97785B1/pl unknown
- 1975-06-30 HU HU75EI00000632A patent/HU172941B/hu unknown
- 1975-06-30 AT AT499475A patent/AT344158B/de not_active IP Right Cessation
- 1975-06-30 CH CH849875A patent/CH617428A5/de not_active IP Right Cessation
- 1975-06-30 SE SE7507482A patent/SE415254B/xx unknown
- 1975-07-01 SU SU752149409A patent/SU786892A3/ru active
- 1975-07-01 ES ES439049A patent/ES439049A1/es not_active Expired
- 1975-07-01 DD DD186999A patent/DD121109A5/xx unknown
- 1975-07-01 AR AR259433A patent/AR212431A1/es active
- 1975-07-01 FR FR7520653A patent/FR2276821A1/fr active Granted
- 1975-07-01 NL NL7507840A patent/NL7507840A/xx not_active Application Discontinuation
- 1975-07-01 BG BG030436A patent/BG27083A3/xx unknown
-
1977
- 1977-11-11 PH PH20425A patent/PH14623A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR212431A1 (es) | 1978-07-14 |
| FR2276821B1 (is") | 1982-03-05 |
| ES439049A1 (es) | 1977-05-16 |
| RO68748A (ro) | 1980-06-15 |
| IL47587A0 (en) | 1975-08-31 |
| DD121109A5 (is") | 1976-07-12 |
| SE415254B (sv) | 1980-09-22 |
| AT344158B (de) | 1978-07-10 |
| AU8253675A (en) | 1977-01-06 |
| DK292175A (is") | 1976-01-02 |
| DE2528846A1 (de) | 1976-01-22 |
| IL47587A (en) | 1978-08-31 |
| DK140313B (da) | 1979-07-30 |
| PH14623A (en) | 1981-10-12 |
| SE7507482L (sv) | 1976-01-02 |
| CA1026335A (en) | 1978-02-14 |
| BG27083A3 (bg) | 1979-08-15 |
| GB1511724A (en) | 1978-05-24 |
| IE41394L (en) | 1976-01-01 |
| HU172941B (hu) | 1979-01-28 |
| FR2276821A1 (fr) | 1976-01-30 |
| DK140313C (is") | 1979-12-17 |
| NL7507840A (nl) | 1976-01-05 |
| CH617428A5 (en) | 1980-05-30 |
| IE41394B1 (en) | 1979-12-19 |
| SU786892A3 (ru) | 1980-12-07 |
| JPS51125078A (en) | 1976-11-01 |
| ATA499475A (de) | 1977-11-15 |
| YU164075A (en) | 1982-02-28 |
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