SU576927A3 - Способ получени гетероциклических амидов или их солей - Google Patents
Способ получени гетероциклических амидов или их солейInfo
- Publication number
- SU576927A3 SU576927A3 SU7402020311A SU2020311A SU576927A3 SU 576927 A3 SU576927 A3 SU 576927A3 SU 7402020311 A SU7402020311 A SU 7402020311A SU 2020311 A SU2020311 A SU 2020311A SU 576927 A3 SU576927 A3 SU 576927A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- yield
- prepared
- aminomethyl
- acetamidonicotinic
- Prior art date
Links
- -1 heterocyclic amides Chemical class 0.000 title description 15
- 238000000034 method Methods 0.000 title description 5
- 150000003839 salts Chemical class 0.000 title description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- RXSLHYTZMIUANX-UHFFFAOYSA-N 6-acetamidopyridine-3-carboxylic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=N1 RXSLHYTZMIUANX-UHFFFAOYSA-N 0.000 description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- ZLWYEPMDOUQDBW-UHFFFAOYSA-N 6-aminonicotinamide Chemical compound NC(=O)C1=CC=C(N)N=C1 ZLWYEPMDOUQDBW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DXDVIHWHNZVPOK-UHFFFAOYSA-N (1-cyclopropylpyrrolidin-2-yl)methanamine Chemical compound NCC1CCCN1C1CC1 DXDVIHWHNZVPOK-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GOLVGZOPWLLUSF-UHFFFAOYSA-N 1-ethylpyrrolidin-3-amine Chemical compound CCN1CCC(N)C1 GOLVGZOPWLLUSF-UHFFFAOYSA-N 0.000 description 1
- ZGZHNQPTNCGKHS-UHFFFAOYSA-N 1-n,1-n-diethylpropane-1,2-diamine Chemical compound CCN(CC)CC(C)N ZGZHNQPTNCGKHS-UHFFFAOYSA-N 0.000 description 1
- ZENKESXKWBIZCV-UHFFFAOYSA-N 2,2,4,4-tetrafluoro-1,3-benzodioxin-6-amine Chemical group O1C(F)(F)OC(F)(F)C2=CC(N)=CC=C21 ZENKESXKWBIZCV-UHFFFAOYSA-N 0.000 description 1
- KRKPMLZTPRQPTR-UHFFFAOYSA-N 2-acetamidopyridine-3-carboxylic acid Chemical compound CC(=O)NC1=NC=CC=C1C(O)=O KRKPMLZTPRQPTR-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- PKTHUBCDDJVKKA-UHFFFAOYSA-N 2-morpholin-4-ylpropan-1-amine Chemical compound NCC(C)N1CCOCC1 PKTHUBCDDJVKKA-UHFFFAOYSA-N 0.000 description 1
- UNIIVAXJUCKZHT-UHFFFAOYSA-N 2-piperidin-1-ylpropan-1-amine Chemical compound NCC(C)N1CCCCC1 UNIIVAXJUCKZHT-UHFFFAOYSA-N 0.000 description 1
- IHHNZPGRBWIKFD-UHFFFAOYSA-N 3-phenyl-3-pyrrolidin-1-ylpropan-1-amine Chemical compound C=1C=CC=CC=1C(CCN)N1CCCC1 IHHNZPGRBWIKFD-UHFFFAOYSA-N 0.000 description 1
- WIPXSOUVAVFXOE-UHFFFAOYSA-N 6-acetamido-n-[(1-ethylpyrrolidin-2-yl)methyl]pyridine-3-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=CC=C(NC(C)=O)N=C1 WIPXSOUVAVFXOE-UHFFFAOYSA-N 0.000 description 1
- FPEXFEYADOCESH-UHFFFAOYSA-N 6-acetamidopyridine-3-carbonyl chloride;hydrochloride Chemical compound Cl.CC(=O)NC1=CC=C(C(Cl)=O)C=N1 FPEXFEYADOCESH-UHFFFAOYSA-N 0.000 description 1
- JTINEEGUDYGYKI-UHFFFAOYSA-N 6-amino-n-(2-morpholin-4-ylpropyl)pyridine-3-carboxamide Chemical compound C1COCCN1C(C)CNC(=O)C1=CC=C(N)N=C1 JTINEEGUDYGYKI-UHFFFAOYSA-N 0.000 description 1
- ZUWPGRPULUSXOT-UHFFFAOYSA-N 6-amino-n-[(1-cyclohexylpyrrolidin-2-yl)methyl]pyridine-3-carboxamide Chemical compound C1=NC(N)=CC=C1C(=O)NCC1N(C2CCCCC2)CCC1 ZUWPGRPULUSXOT-UHFFFAOYSA-N 0.000 description 1
- PKGOOIBPIZWNHH-UHFFFAOYSA-N 6-amino-n-[(1-ethylpyrrolidin-2-yl)methyl]pyridine-3-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=CC=C(N)N=C1 PKGOOIBPIZWNHH-UHFFFAOYSA-N 0.000 description 1
- WWZJYQOGUACHLS-UHFFFAOYSA-N 6-amino-n-[2-(diethylamino)propyl]pyridine-3-carboxamide Chemical compound CCN(CC)C(C)CNC(=O)C1=CC=C(N)N=C1 WWZJYQOGUACHLS-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- OLXSIFMDQTZGKU-UHFFFAOYSA-N [1-(3-phenylprop-2-enyl)pyrrolidin-2-yl]methanamine Chemical compound NCC1N(CCC1)CC=CC1=CC=CC=C1 OLXSIFMDQTZGKU-UHFFFAOYSA-N 0.000 description 1
- LTQMRPNCLOKBQW-UHFFFAOYSA-N [1-(3-phenylpropyl)pyrrolidin-2-yl]methanamine Chemical compound NCC1CCCN1CCCC1=CC=CC=C1 LTQMRPNCLOKBQW-UHFFFAOYSA-N 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N alpha-aminopyridine Natural products NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2084273A GB1428493A (en) | 1973-05-02 | 1973-05-02 | Heterocyclic amides processes for their preparation and pharma ceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU576927A3 true SU576927A3 (ru) | 1977-10-15 |
Family
ID=10152644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7402020311A SU576927A3 (ru) | 1973-05-02 | 1974-04-30 | Способ получени гетероциклических амидов или их солей |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3970661A (enExample) |
| JP (1) | JPS523937B2 (enExample) |
| CA (1) | CA1025865A (enExample) |
| CH (1) | CH590234A5 (enExample) |
| FR (1) | FR2227866B1 (enExample) |
| GB (1) | GB1428493A (enExample) |
| SE (1) | SE401502B (enExample) |
| SU (1) | SU576927A3 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2663026B1 (fr) * | 1990-06-07 | 1992-08-07 | Synthelabo | Derives de [(1-arylpyrrolidin-2-yl) methyl] piperazine, leur preparation et leur application en therapeutique. |
| FR2684374B1 (fr) * | 1991-12-02 | 1995-05-19 | Synthelabo | Derives substitues de 1-[(1-arylpyrrolidin-2-yl)methyl]piperazine, leur preparation et leur application en therapeutique. |
| US7176310B1 (en) | 2002-04-09 | 2007-02-13 | Ucb Sa | Pyrimidinecarboxamide derivatives and their use as anti-inflammatory agents |
| FR2928070A1 (fr) * | 2008-02-27 | 2009-09-04 | Sumitomo Chemical Co | Composition agricole, utilisation d'un compose pour sa production et procede pour matriser ou prevenir les maladies des plantes. |
| US20170247326A1 (en) * | 2014-09-10 | 2017-08-31 | Epizyme, Inc. | Substituted Pyrrolidine Carboxamide Compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3105072A (en) * | 1963-09-24 | Preparation thereof |
-
1973
- 1973-05-02 GB GB2084273A patent/GB1428493A/en not_active Expired
-
1974
- 1974-04-26 CH CH577274A patent/CH590234A5/xx not_active IP Right Cessation
- 1974-04-26 CA CA198,244A patent/CA1025865A/fr not_active Expired
- 1974-04-29 SE SE7405743A patent/SE401502B/xx unknown
- 1974-04-30 SU SU7402020311A patent/SU576927A3/ru active
- 1974-04-30 FR FR7414933A patent/FR2227866B1/fr not_active Expired
- 1974-05-01 US US05/465,931 patent/US3970661A/en not_active Expired - Lifetime
- 1974-05-01 JP JP49049238A patent/JPS523937B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2227866B1 (enExample) | 1978-06-30 |
| SE401502B (sv) | 1978-05-16 |
| JPS523937B2 (enExample) | 1977-01-31 |
| US3970661A (en) | 1976-07-20 |
| JPS5018472A (enExample) | 1975-02-26 |
| FR2227866A1 (enExample) | 1974-11-29 |
| GB1428493A (en) | 1976-03-17 |
| CA1025865A (fr) | 1978-02-07 |
| DE2419535A1 (de) | 1974-12-12 |
| DE2419535B2 (de) | 1977-01-13 |
| CH590234A5 (enExample) | 1977-07-29 |
| AU6842774A (en) | 1975-11-06 |
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