SU609464A3 - Способ получени производных -/2-пирролидинилметил/ бензамидов или их солей - Google Patents
Способ получени производных -/2-пирролидинилметил/ бензамидов или их солейInfo
- Publication number
- SU609464A3 SU609464A3 SU2112487A SU2112487A SU609464A3 SU 609464 A3 SU609464 A3 SU 609464A3 SU 2112487 A SU2112487 A SU 2112487A SU 2112487 A SU2112487 A SU 2112487A SU 609464 A3 SU609464 A3 SU 609464A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- filtered
- washed
- water
- methoxy
- mixture
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- 229940054066 benzamide antipsychotics Drugs 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- SDSNCRLGLMMTNF-UHFFFAOYSA-N n-(pyrrolidin-2-ylmethyl)benzamide Chemical class C=1C=CC=CC=1C(=O)NCC1CCCN1 SDSNCRLGLMMTNF-UHFFFAOYSA-N 0.000 claims description 3
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 12
- 238000001816 cooling Methods 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 10
- 239000000047 product Substances 0.000 claims 9
- 239000013078 crystal Substances 0.000 claims 7
- 239000002904 solvent Substances 0.000 claims 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- -1 aryl dichlorophosphites Chemical class 0.000 claims 6
- 229910052759 nickel Inorganic materials 0.000 claims 5
- AUKXFNABVHIUAC-UHFFFAOYSA-N pyrrolidin-2-ylmethylamine Chemical compound NCC1CCCN1 AUKXFNABVHIUAC-UHFFFAOYSA-N 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 4
- 239000002244 precipitate Substances 0.000 claims 4
- 235000011121 sodium hydroxide Nutrition 0.000 claims 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 238000009835 boiling Methods 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- 238000003756 stirring Methods 0.000 claims 3
- OEYAFMGVIFWPQI-UHFFFAOYSA-N (1-benzylpyrrolidin-2-yl)methanamine Chemical compound NCC1CCCN1CC1=CC=CC=C1 OEYAFMGVIFWPQI-UHFFFAOYSA-N 0.000 claims 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 238000005576 amination reaction Methods 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical class C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- TZOCBFJIISELCS-UHFFFAOYSA-N 2,3-dimethoxy-5-sulfamoylbenzoyl chloride Chemical compound COC1=CC(S(N)(=O)=O)=CC(C(Cl)=O)=C1OC TZOCBFJIISELCS-UHFFFAOYSA-N 0.000 claims 1
- RCFGFTLCCWRMTI-UHFFFAOYSA-N 2-methoxy-5-methylsulfonylbenzoyl chloride Chemical compound COC1=CC=C(S(C)(=O)=O)C=C1C(Cl)=O RCFGFTLCCWRMTI-UHFFFAOYSA-N 0.000 claims 1
- OLJXRTRRJSMURJ-UHFFFAOYSA-N 4-amino-2-methoxybenzoic acid Chemical compound COC1=CC(N)=CC=C1C(O)=O OLJXRTRRJSMURJ-UHFFFAOYSA-N 0.000 claims 1
- NBFYWQQYIJTQQV-UHFFFAOYSA-N 5-ethylsulfonyl-2-methoxybenzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(C(O)=O)=C1 NBFYWQQYIJTQQV-UHFFFAOYSA-N 0.000 claims 1
- GSFGGUVBFJQNQQ-UHFFFAOYSA-N 5-ethylsulfonyl-2-methoxybenzoyl chloride Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(C(Cl)=O)=C1 GSFGGUVBFJQNQQ-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical class OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 1
- ZQSFLXDMGBSJKV-UHFFFAOYSA-N ethyl 2-methoxy-5-sulfamoylbenzoate Chemical compound CCOC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC ZQSFLXDMGBSJKV-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 150000007928 imidazolide derivatives Chemical class 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 1
- 235000019341 magnesium sulphate Nutrition 0.000 claims 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 claims 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims 1
- 125000003431 oxalo group Chemical group 0.000 claims 1
- 229920005862 polyol Polymers 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 239000000126 substance 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
-
- 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
-
- 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)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7407535A FR2262966A1 (fr) | 1974-03-05 | 1974-03-05 | Nouveau benzamide hétérocyclique et son procédé de fabrication |
| FR7503800A FR2299863B1 (fr) | 1975-02-07 | 1975-02-07 | Nouveaux N-(Z-pyrrolidiny alkyl) benzamides substitués, leurs dérivés et leur procédé de préparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SU609464A1 SU609464A1 (ru) | 1978-05-30 |
| SU609464A3 true SU609464A3 (ru) | 1978-05-30 |
Family
ID=26218210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2112487A SU609464A3 (ru) | 1974-03-05 | 1975-03-04 | Способ получени производных -/2-пирролидинилметил/ бензамидов или их солей |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS6015616B2 (enExample) |
| AR (1) | AR206621A1 (enExample) |
| AT (1) | AT358570B (enExample) |
| BG (1) | BG24666A3 (enExample) |
| CA (1) | CA1047504A (enExample) |
| CH (1) | CH605794A5 (enExample) |
| CS (1) | CS189692B2 (enExample) |
| DD (1) | DD119420A5 (enExample) |
| DE (1) | DE2507989A1 (enExample) |
| DK (1) | DK145377C (enExample) |
| EG (1) | EG12577A (enExample) |
| ES (1) | ES435274A1 (enExample) |
| FI (1) | FI750620A7 (enExample) |
| GB (1) | GB1466822A (enExample) |
| HK (1) | HK14078A (enExample) |
| HU (1) | HU170637B (enExample) |
| IE (1) | IE40818B1 (enExample) |
| IL (1) | IL46696A (enExample) |
| LU (1) | LU71949A1 (enExample) |
| NL (1) | NL7502608A (enExample) |
| NO (1) | NO750713L (enExample) |
| OA (1) | OA04966A (enExample) |
| PH (1) | PH14197A (enExample) |
| PL (1) | PL97091B1 (enExample) |
| RO (2) | RO72844A (enExample) |
| SE (1) | SE411754B (enExample) |
| SU (1) | SU609464A3 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ186175A (en) * | 1977-01-27 | 1980-03-05 | Shionogi & Co | Meta-sulphonamidobenzamide derivatives |
| SE8503054D0 (sv) * | 1985-06-19 | 1985-06-19 | Astra Laekemedel Ab | Catecholcarboxamides |
| US4772459A (en) * | 1986-09-09 | 1988-09-20 | Erbamont, Inc. | Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein |
| EP0314483A1 (en) * | 1987-10-29 | 1989-05-03 | Erbamont, Inc. | Preparation of benzamides |
| FR2699533A1 (fr) * | 1992-12-21 | 1994-06-24 | Mouhtaram Mohamed | Dérivés de N-((1,4-dialkyl-6-arylpipérazine-2-yl)méthyl)benzamides. (Isomères cis et trans) Propriétés pharmacologiques et applications. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3078497A (en) * | 1960-12-29 | 1963-02-26 | Leeds And Mieallef | Dispensing containers |
-
1975
- 1975-02-24 IL IL46696A patent/IL46696A/en unknown
- 1975-02-25 DE DE19752507989 patent/DE2507989A1/de not_active Withdrawn
- 1975-02-26 GB GB809575A patent/GB1466822A/en not_active Expired
- 1975-03-03 SE SE7502342A patent/SE411754B/sv not_active IP Right Cessation
- 1975-03-03 AT AT160775A patent/AT358570B/de not_active IP Right Cessation
- 1975-03-03 EG EG109/75A patent/EG12577A/ar active
- 1975-03-03 LU LU71949A patent/LU71949A1/fr unknown
- 1975-03-04 CA CA221,240A patent/CA1047504A/en not_active Expired
- 1975-03-04 FI FI750620A patent/FI750620A7/fi not_active Application Discontinuation
- 1975-03-04 HU HUSO1137A patent/HU170637B/hu not_active IP Right Cessation
- 1975-03-04 OA OA55430A patent/OA04966A/fr unknown
- 1975-03-04 NO NO750713A patent/NO750713L/no unknown
- 1975-03-04 DK DK86975A patent/DK145377C/da active
- 1975-03-04 SU SU2112487A patent/SU609464A3/ru active
- 1975-03-04 BG BG029148A patent/BG24666A3/bg unknown
- 1975-03-04 ES ES435274A patent/ES435274A1/es not_active Expired
- 1975-03-04 IE IE457/75A patent/IE40818B1/en unknown
- 1975-03-04 CS CS751445A patent/CS189692B2/cs unknown
- 1975-03-05 RO RO7581558A patent/RO72844A/ro unknown
- 1975-03-05 RO RO7588831A patent/RO70647A/ro unknown
- 1975-03-05 JP JP50027573A patent/JPS6015616B2/ja not_active Expired
- 1975-03-05 NL NL7502608A patent/NL7502608A/nl not_active Application Discontinuation
- 1975-03-05 CH CH279975A patent/CH605794A5/fr not_active IP Right Cessation
- 1975-03-05 PL PL1975178533A patent/PL97091B1/pl unknown
- 1975-03-05 DD DD184579A patent/DD119420A5/de unknown
- 1975-04-04 AR AR257837A patent/AR206621A1/es active
-
1977
- 1977-08-22 PH PH20152A patent/PH14197A/en unknown
-
1978
- 1978-03-16 HK HK140/78A patent/HK14078A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU520041A3 (ru) | Способ получени амидов ароматических карбоновых кислот или их солей | |
| US2441498A (en) | Alkyl glycinanilides | |
| SU602116A3 (ru) | Способ получени замещенных (1-бензилпирролидинил-2-алкил)бензамидов или их кислых или аммонийных солей или их правовращающих или левовращающих изомеров | |
| US2654738A (en) | Organic derivatives of phosphonic acids and method of preparing the same | |
| SU609464A3 (ru) | Способ получени производных -/2-пирролидинилметил/ бензамидов или их солей | |
| US3432522A (en) | Pyrrole-2-carboxamido alkylene amidines | |
| SU555847A3 (ru) | Способ получени 2,5-дизамещенных бензамидов или их солей | |
| US2455894A (en) | Production of 1-mono-and 1, 2-disubstituted-3-cyanoguanidines | |
| SU695556A3 (ru) | Способ получени -/1-аллил-2пирролидилметил/-2,3-диметокси-5сульфамоилбензамида или его солей | |
| SU858568A3 (ru) | Способ получени производных пурина или их солей | |
| CA1055502A (en) | Process for the preparation of 2,5-disubstituted benzamides | |
| NO135092B (enExample) | ||
| US3378592A (en) | Process for the production of 3, 4-dihydroxybenzyloxyaminehydrobromide | |
| US4804765A (en) | Process for synthesizing N-[(1'-allyl-2'pyrrolidinyl) methyl]2-methoxy-4,5-azimidobenzamide | |
| US3433802A (en) | 3-(n-lower-alkylanilino)pyrrolidines | |
| SU512697A3 (ru) | Способ получени бензиламинов | |
| US2535971A (en) | 1-carbalkoxy-4-substituted piperazines | |
| US2413833A (en) | Substituted 4,4'-diaminodiphenyl sulfones and process of making same | |
| US2883381A (en) | New process for the production of hy- | |
| SU468405A3 (ru) | Способ получени тиоловых эфиров гуанидинорганических кислот | |
| RU2744470C1 (ru) | Способ получения изотиобарбамина | |
| US2662885A (en) | Antihistamine compounds | |
| SU430554A1 (ru) | Способ получения производных 2,3-бензоксазепина | |
| US2517496A (en) | Preparation of symmetrical monoaminodihydroxytoluene | |
| SU398038A1 (ru) | Способ получения производных |