SU522791A3 - Способ получени производных 3-алкил-4-сульфамоиланилина - Google Patents
Способ получени производных 3-алкил-4-сульфамоиланилинаInfo
- Publication number
- SU522791A3 SU522791A3 SU1935342A SU1935342A SU522791A3 SU 522791 A3 SU522791 A3 SU 522791A3 SU 1935342 A SU1935342 A SU 1935342A SU 1935342 A SU1935342 A SU 1935342A SU 522791 A3 SU522791 A3 SU 522791A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- group
- residue
- acid
- alkyl
- tetrazolyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000002253 acid Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 125000002560 nitrile group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- OEDSWHXVAAHNMR-UHFFFAOYSA-N 2-bromo-4-propan-2-yl-5-sulfamoylbenzoic acid Chemical compound CC(C)C1=CC(Br)=C(C(O)=O)C=C1S(N)(=O)=O OEDSWHXVAAHNMR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000002633 imido ester group Chemical group 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000001568 sexual effect Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZQSLNSHMUQXSQJ-UHFFFAOYSA-N 2-(furan-2-yl)ethanamine Chemical compound NCCC1=CC=CO1 ZQSLNSHMUQXSQJ-UHFFFAOYSA-N 0.000 description 1
- UETYGBQTKZBKPM-UHFFFAOYSA-N 2-(furan-2-ylmethylamino)-4-propan-2-yl-5-sulfamoylbenzoic acid Chemical compound C1=C(S(N)(=O)=O)C(C(C)C)=CC(NCC=2OC=CC=2)=C1C(O)=O UETYGBQTKZBKPM-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- HPHRQHMADUKEHJ-UHFFFAOYSA-N 2-bromo-4-butyl-5-sulfamoylbenzoic acid Chemical compound CCCCC1=CC(Br)=C(C(O)=O)C=C1S(N)(=O)=O HPHRQHMADUKEHJ-UHFFFAOYSA-N 0.000 description 1
- KEUJHKJYVMHKHE-UHFFFAOYSA-N 2-bromo-4-ethyl-5-sulfamoylbenzoic acid Chemical compound CCC1=CC(Br)=C(C(O)=O)C=C1S(N)(=O)=O KEUJHKJYVMHKHE-UHFFFAOYSA-N 0.000 description 1
- UKUULYMIHRLDEG-UHFFFAOYSA-N 4-butyl-2-[2-(furan-2-yl)ethylamino]-5-sulfamoylbenzoic acid Chemical compound C1=C(S(N)(=O)=O)C(CCCC)=CC(NCCC=2OC=CC=2)=C1C(O)=O UKUULYMIHRLDEG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 240000008866 Ziziphus nummularia Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001409 amidines Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-M chlorosulfate Chemical compound [O-]S(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-M 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- -1 ethyl acetate ester Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2232457A DE2232457A1 (de) | 1972-07-01 | 1972-07-01 | Neue 3-alkyl-4-sulfamoylanilinderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU522791A3 true SU522791A3 (ru) | 1976-07-25 |
Family
ID=5849465
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1935342A SU522791A3 (ru) | 1972-07-01 | 1973-06-29 | Способ получени производных 3-алкил-4-сульфамоиланилина |
| SU2073186A SU520913A3 (ru) | 1972-07-01 | 1974-11-10 | Способ получени производных 3-алкил-4-сульфамоиланилина |
| SU2074752A SU541429A3 (ru) | 1972-07-01 | 1974-11-12 | Способ получени производных 3-алкил-4-сульфамоиланилина или их солей |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2073186A SU520913A3 (ru) | 1972-07-01 | 1974-11-10 | Способ получени производных 3-алкил-4-сульфамоиланилина |
| SU2074752A SU541429A3 (ru) | 1972-07-01 | 1974-11-12 | Способ получени производных 3-алкил-4-сульфамоиланилина или их солей |
Country Status (20)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2611705A1 (de) * | 1976-03-18 | 1977-09-22 | Josef Dipl Chem Dr Rer N Klosa | N-5-(nitrofurfuryliden-)-1-amino- hydantoin enthaltende kristalloesungsmittel |
| DE3006686A1 (de) * | 1980-02-22 | 1981-08-27 | Hoechst Ag, 6000 Frankfurt | 5-sulfamoyl-orthanilsaeuren, verfahren zu ihrer herstellung und ihre verwendung als heilmittel |
| DE3009229A1 (de) * | 1980-03-11 | 1981-10-15 | Hoechst Ag, 6000 Frankfurt | 2,4-diamino-5-sulfamoylbenzolsulfosaeuren und verfahen zu ihrer herstellung |
| DE3034664A1 (de) * | 1980-09-13 | 1982-05-06 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verbessertes verfahren zur herstellung von 5-(4'-chlor-5'-sulfamoyl-2'-thenylamino)-phenyl-tetrazol |
| DE3101960A1 (de) * | 1981-01-22 | 1982-09-02 | Hoechst Ag, 6000 Frankfurt | "basisch substituierte anthranilsaeuren, verfahren zu ihrer herstellung und ihre verwendung" |
| JPS5846881U (ja) * | 1981-09-28 | 1983-03-29 | カルソニックカンセイ株式会社 | 自動車用空気調和装置におけるコンプレツサの取付構造 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2910488A (en) * | 1958-01-22 | 1959-10-27 | Merck & Co Inc | Aniline derivatives |
| FR1261176A (fr) * | 1959-01-09 | 1961-05-19 | Merck & Co Inc | Procédé de fabrication de dérivés de l'aniline tels que la 2-carboxy-5-chloro-4-sulfamylacétanilide |
| US3565920A (en) * | 1966-12-29 | 1971-02-23 | Ciba Geigy Corp | 5-sulfamyl-anthranilic acids |
| DE1815922C3 (de) * | 1968-12-20 | 1979-04-26 | Boehringer Mannheim Gmbh, 6800 Mannheim | 5-Phenyltetrazol-Derivate |
| DE2034986A1 (de) * | 1970-07-15 | 1972-01-20 | Boehnnger Mannheim GmbH, 6800 Mann heim Waldhof | 4 Sulfamoyl m toluidin Derivate |
-
1972
- 1972-07-01 DE DE2232457A patent/DE2232457A1/de active Pending
-
1973
- 1973-06-18 US US371212A patent/US3914219A/en not_active Expired - Lifetime
- 1973-06-24 IL IL42590A patent/IL42590A/en unknown
- 1973-06-25 CS CS8575A patent/CS178141B2/cs unknown
- 1973-06-25 CS CS4546A patent/CS178132B2/cs unknown
- 1973-06-25 GB GB3005973A patent/GB1373337A/en not_active Expired
- 1973-06-25 DD DD171800A patent/DD104783A5/xx unknown
- 1973-06-25 CS CS8576A patent/CS178142B2/cs unknown
- 1973-06-26 ES ES416306A patent/ES416306A1/es not_active Expired
- 1973-06-26 IE IE1063/73A patent/IE37851B1/xx unknown
- 1973-06-27 ZA ZA734374A patent/ZA734374B/xx unknown
- 1973-06-27 CH CH939773A patent/CH584684A5/xx not_active IP Right Cessation
- 1973-06-27 CH CH816976A patent/CH584195A5/xx not_active IP Right Cessation
- 1973-06-27 CH CH816876A patent/CH584194A5/xx not_active IP Right Cessation
- 1973-06-29 AT AT729474A patent/AT326631B/de not_active IP Right Cessation
- 1973-06-29 SU SU1935342A patent/SU522791A3/ru active
- 1973-06-29 AT AT577573A patent/AT326104B/de not_active IP Right Cessation
- 1973-06-29 FR FR7323850A patent/FR2190455B1/fr not_active Expired
- 1973-06-29 AT AT729374A patent/ATA729374A/de unknown
- 1973-06-29 SE SE7309204A patent/SE404694B/xx unknown
- 1973-06-29 HU HUBO1443A patent/HU165886B/hu unknown
- 1973-06-29 NL NL737309119A patent/NL149802B/xx unknown
- 1973-06-29 AR AR248853A patent/AR199213A1/es active
- 1973-06-29 AT AT729374A patent/AT326630B/de not_active IP Right Cessation
- 1973-06-30 PL PL1973163738A patent/PL85216B1/pl unknown
- 1973-07-02 JP JP48074661A patent/JPS4942642A/ja active Pending
- 1973-07-02 AU AU57623/73A patent/AU471260B2/en not_active Expired
-
1974
- 1974-01-23 AR AR252046A patent/AR199327A1/es active
- 1974-01-23 AR AR252045A patent/AR199326A1/es active
- 1974-11-10 SU SU2073186A patent/SU520913A3/ru active
- 1974-11-12 SU SU2074752A patent/SU541429A3/ru active
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