CS226183B2 - Method of preparing n-ethyl-2-(2,6-dialkoxybenzamidomethyl)-pyrrolidine derivatives - Google Patents
Method of preparing n-ethyl-2-(2,6-dialkoxybenzamidomethyl)-pyrrolidine derivatives Download PDFInfo
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- CS226183B2 CS226183B2 CS791902A CS190279A CS226183B2 CS 226183 B2 CS226183 B2 CS 226183B2 CS 791902 A CS791902 A CS 791902A CS 190279 A CS190279 A CS 190279A CS 226183 B2 CS226183 B2 CS 226183B2
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- Czechoslovakia
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- 238000000034 method Methods 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 238000002360 preparation method Methods 0.000 claims abstract description 17
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- 150000003839 salts Chemical class 0.000 claims abstract description 11
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- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
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- 150000002367 halogens Chemical class 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- YKRCBICZQYVBCZ-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-2,6-dimethoxybenzamide;hydrochloride Chemical compound Cl.CCN1CCCC1CNC(=O)C1=C(OC)C=CC=C1OC YKRCBICZQYVBCZ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 101150006061 neur gene Proteins 0.000 description 1
- 230000001537 neural effect Effects 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- BGRJTUBHPOOWDU-UHFFFAOYSA-N sulpiride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7803411A SE411118B (sv) | 1978-03-23 | 1978-03-23 | Ett forfarande for framstellning av 2,6-dialkoxibensamider med terapentiska egenskaper |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS226183B2 true CS226183B2 (en) | 1984-03-19 |
Family
ID=20334412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS791902A CS226183B2 (en) | 1978-03-23 | 1979-03-22 | Method of preparing n-ethyl-2-(2,6-dialkoxybenzamidomethyl)-pyrrolidine derivatives |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4232037A (no) |
| EP (1) | EP0004831B1 (no) |
| JP (1) | JPS585910B2 (no) |
| AT (1) | AT374173B (no) |
| AU (1) | AU525475B2 (no) |
| CA (1) | CA1101873A (no) |
| CS (1) | CS226183B2 (no) |
| DD (1) | DD143605A5 (no) |
| DE (1) | DE2964774D1 (no) |
| DK (1) | DK157844C (no) |
| ES (1) | ES478871A1 (no) |
| FI (1) | FI73979C (no) |
| HK (1) | HK77085A (no) |
| HU (1) | HU177793B (no) |
| IE (1) | IE48491B1 (no) |
| LT (1) | LT2246B (no) |
| LU (1) | LU88308I2 (no) |
| MX (1) | MX9203148A (no) |
| MY (1) | MY8500407A (no) |
| NL (1) | NL930052I2 (no) |
| NO (1) | NO152414C (no) |
| NZ (1) | NZ189935A (no) |
| SE (1) | SE411118B (no) |
| SG (1) | SG51885G (no) |
| SU (1) | SU818481A3 (no) |
| ZA (1) | ZA79964B (no) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8101536L (sv) * | 1981-03-11 | 1982-09-12 | Astra Laekemedel Ab | Bensamid-derivat |
| US4470977A (en) * | 1981-06-04 | 1984-09-11 | Adria Laboratories, Inc. | Antiemetic and antipsychotic agents |
| SE8205135D0 (sv) * | 1982-09-09 | 1982-09-09 | Astra Laekemedel Ab | Benzamido-derivatives |
| SE8400478D0 (sv) * | 1984-01-31 | 1984-01-31 | Astra Laekemedel Ab | Oxysalicylamido derivatives |
| US5240957A (en) * | 1984-01-31 | 1993-08-31 | Astra Lakemedel Akteibolag | Oxysalicylamido derivatives |
| SE8503054D0 (sv) * | 1985-06-19 | 1985-06-19 | Astra Laekemedel Ab | Catecholcarboxamides |
| DE3629598A1 (de) * | 1986-08-30 | 1988-03-03 | Boehringer Ingelheim Kg | 3-brom-2,6-dimethoxibenzamide, ihre herstellung und verwendung |
| US4772459A (en) * | 1986-09-09 | 1988-09-20 | Erbamont, Inc. | Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein |
| US4751236A (en) * | 1987-05-20 | 1988-06-14 | Avihou Mishniot | Method for treating genital herpes |
| US5154913A (en) * | 1987-11-19 | 1992-10-13 | Vanderbilt University | Radioiodinated benzamines method of their use as radioimaging agents |
| US5231099A (en) * | 1991-04-15 | 1993-07-27 | Du Pont Merck Pharmaceutical Company | Use of sigma receptor antagonists to enhance the effects of antipsychotic drugs |
| WO1993002036A1 (en) * | 1991-07-15 | 1993-02-04 | Merck & Co., Inc. | Novel process for aromatic bromination |
| US5248817A (en) * | 1991-07-15 | 1993-09-28 | Merck & Co., Inc. | Process for aromatic bromination |
| CN104058956A (zh) * | 2014-06-04 | 2014-09-24 | 蚌埠团结日用化学有限公司 | 3-溴-2，6二甲氧基苯甲酸合成的生产工艺 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD67123A (no) * | ||||
| US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
| FR5916M (no) * | 1966-01-21 | 1968-05-06 | ||
| BE695272A (no) * | 1967-03-09 | 1967-09-11 | ||
| US3862139A (en) * | 1972-06-23 | 1975-01-21 | Delmar Chem | Heterocyclic benzamide compounds |
| IT1070992B (it) * | 1973-12-21 | 1985-04-02 | Italfarmaco Spa | Processo per la preparazione della i etil 2 2 metossi 5 sulfamoil benzamidometil pirrolidina |
| CH605793A5 (fr) * | 1974-03-05 | 1978-10-13 | Soc Et Scient Et Ind | Procédé de préparation de nouveaux N-(1benzylpyrrollidinil 2-alkyl) benzamides substitués |
| FR2294698A1 (fr) * | 1974-12-18 | 1976-07-16 | Synthelabo | Nouveaux derives des methoxy-2 benzamides substitues, leurs sels, leur preparation et les medicaments qui en renferment |
| SE412908B (sv) * | 1974-12-18 | 1980-03-24 | Synthelabo | Forfarande for framstellning av terapeutiskt aktiva 2-metoxibensamider innehallande en pyrrolidin- eller en piperidinrest |
-
1978
- 1978-03-23 SE SE7803411A patent/SE411118B/sv unknown
-
1979
- 1979-02-28 ZA ZA79964A patent/ZA79964B/xx unknown
- 1979-03-01 CA CA322,555A patent/CA1101873A/en not_active Expired
- 1979-03-05 DE DE7979850013T patent/DE2964774D1/de not_active Expired
- 1979-03-05 EP EP79850013A patent/EP0004831B1/en not_active Expired
- 1979-03-08 US US06/018,784 patent/US4232037A/en not_active Expired - Lifetime
- 1979-03-19 NZ NZ189935A patent/NZ189935A/en unknown
- 1979-03-19 AU AU45219/79A patent/AU525475B2/en not_active Ceased
- 1979-03-19 FI FI790922A patent/FI73979C/fi not_active IP Right Cessation
- 1979-03-20 NO NO790934A patent/NO152414C/no unknown
- 1979-03-22 HU HU79AA924A patent/HU177793B/hu not_active IP Right Cessation
- 1979-03-22 CS CS791902A patent/CS226183B2/cs unknown
- 1979-03-22 DK DK117779A patent/DK157844C/da not_active IP Right Cessation
- 1979-03-22 DD DD79211750A patent/DD143605A5/de not_active IP Right Cessation
- 1979-03-22 ES ES478871A patent/ES478871A1/es not_active Expired
- 1979-03-22 SU SU792739699A patent/SU818481A3/ru active
- 1979-03-23 AT AT0217779A patent/AT374173B/de not_active IP Right Cessation
- 1979-03-23 JP JP54033429A patent/JPS585910B2/ja not_active Expired
- 1979-08-08 IE IE630/79A patent/IE48491B1/en not_active IP Right Cessation
-
1985
- 1985-07-01 SG SG518/85A patent/SG51885G/en unknown
- 1985-10-10 HK HK770/85A patent/HK77085A/en not_active IP Right Cessation
- 1985-12-30 MY MY407/85A patent/MY8500407A/xx unknown
-
1992
- 1992-06-23 MX MX9203148A patent/MX9203148A/es unknown
-
1993
- 1993-06-10 NL NL930052C patent/NL930052I2/nl unknown
- 1993-06-16 LU LU88308C patent/LU88308I2/fr unknown
- 1993-09-06 LT LTRP936A patent/LT2246B/xx unknown
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