SE449747B - Forfarande for framstellning av n-/2-//5-/(dimetylamino) metyl/-2-furanylmetyl/-tio/etyl/n'-metyl-2-nitro-1,1-etendiamin (ranitidin) - Google Patents
Forfarande for framstellning av n-/2-//5-/(dimetylamino) metyl/-2-furanylmetyl/-tio/etyl/n'-metyl-2-nitro-1,1-etendiamin (ranitidin)Info
- Publication number
- SE449747B SE449747B SE8100074A SE8100074A SE449747B SE 449747 B SE449747 B SE 449747B SE 8100074 A SE8100074 A SE 8100074A SE 8100074 A SE8100074 A SE 8100074A SE 449747 B SE449747 B SE 449747B
- Authority
- SE
- Sweden
- Prior art keywords
- methyl
- formula
- dimethylamino
- evaporated
- nitro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical class CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 title description 6
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 title description 3
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 title 1
- 229960000620 ranitidine Drugs 0.000 title 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- -1 ethyleneimino group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000002240 furans Chemical class 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 150000003573 thiols Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- BSRMPIUBLXOMPP-UHFFFAOYSA-N 1-n'-(2-chloroethyl)-1-n-methyl-2-nitroethene-1,1-diamine Chemical compound [O-][N+](=O)C=C(NC)NCCCl BSRMPIUBLXOMPP-UHFFFAOYSA-N 0.000 description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 3
- 235000010262 sodium metabisulphite Nutrition 0.000 description 3
- SLQQETBEMPWQFC-UHFFFAOYSA-N 1-N'-(2-chloroethyl)-1-N-methyl-2-nitroethane-1,1-diamine Chemical compound CNC(C[N+]([O-])=O)NCCCl SLQQETBEMPWQFC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Substances OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229940001584 sodium metabisulfite Drugs 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- ZVIREQPONFZPLQ-UHFFFAOYSA-N 1-nitroethenamine Chemical compound NC(=C)[N+]([O-])=O ZVIREQPONFZPLQ-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 description 1
- QCMDPLIQGZLTGJ-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.C(=N)N Chemical compound C(C=C/C(=O)O)(=O)O.C(=N)N QCMDPLIQGZLTGJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KLPXXRDSVDIUIL-UHFFFAOYSA-N [5-[(dimethylamino)methyl]furan-2-yl]methanethiol Chemical compound CN(C)CC1=CC=C(CS)O1 KLPXXRDSVDIUIL-UHFFFAOYSA-N 0.000 description 1
- QNJSCRNVDDKPSI-UHFFFAOYSA-N [5-[(dimethylamino)methyl]furan-2-yl]methanethiol;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CC1=CC=C(CS)O1 QNJSCRNVDDKPSI-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 229940099596 manganese sulfate Drugs 0.000 description 1
- 239000011702 manganese sulphate Substances 0.000 description 1
- 235000007079 manganese sulphate Nutrition 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/12—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8000580 | 1980-01-08 | ||
| GB8000581 | 1980-01-08 | ||
| GB8039336 | 1980-12-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8100074L SE8100074L (sv) | 1981-07-09 |
| SE449747B true SE449747B (sv) | 1987-05-18 |
Family
ID=27260837
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8100074A SE449747B (sv) | 1980-01-08 | 1981-01-08 | Forfarande for framstellning av n-/2-//5-/(dimetylamino) metyl/-2-furanylmetyl/-tio/etyl/n'-metyl-2-nitro-1,1-etendiamin (ranitidin) |
| SE8502780A SE460604B (sv) | 1980-01-08 | 1985-06-05 | Aziridinderivat och foerfarande foer dess framstaellning |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8502780A SE460604B (sv) | 1980-01-08 | 1985-06-05 | Aziridinderivat och foerfarande foer dess framstaellning |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPH02167259A (en, 2012) |
| AR (1) | AR225940A1 (en, 2012) |
| AT (1) | AT376966B (en, 2012) |
| CH (1) | CH650257A5 (en, 2012) |
| DE (1) | DE3100364A1 (en, 2012) |
| DK (1) | DK157865C (en, 2012) |
| ES (1) | ES498389A0 (en, 2012) |
| FI (1) | FI80450C (en, 2012) |
| FR (1) | FR2473044A1 (en, 2012) |
| HU (1) | HU182272B (en, 2012) |
| NL (1) | NL8100068A (en, 2012) |
| PT (1) | PT72320B (en, 2012) |
| SE (2) | SE449747B (en, 2012) |
| YU (1) | YU42372B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3213509A1 (de) * | 1982-04-10 | 1983-10-20 | Basf Ag, 6700 Ludwigshafen | N-substituierte imidazol-derivate, ihre herstellung, diese enthaltende arzneimittel und ihre verwendung |
| YU42819B (en) * | 1982-11-22 | 1988-12-31 | Lek Tovarna Farmacevtskih | Process for preparing n-/2-///5-(dimethyl-amino)-methyl-2-furanyl/methyl/thio/ethyl-n'-methyl-2-nitro-1,1-ethene diamine |
| NL8303965A (nl) * | 1982-12-08 | 1984-07-02 | Degussa | Nieuwe etheendiamine- en guanidine-derivaten; werkwijze voor het bereiden daarvan; geneesmiddelen die ze bevatten; werkwijze voor het bereiden van dergelijke geneesmiddelen; toepassing van de verbindingen voor het bereiden van geneesmiddelen en in de geneeskunde. |
| DE3343884A1 (de) * | 1982-12-08 | 1984-06-14 | Degussa Ag, 6000 Frankfurt | Neue ethendiamin- und guanidin-derivate |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1565966A (en) * | 1976-08-04 | 1980-04-23 | Allen & Hanburys Ltd | Aminoalkyl furan derivatives |
| IL56265A (en) | 1977-12-28 | 1982-08-31 | Om Lab Sa | Process for preparing imidazolyl methylthio guanidine derivatives and a novel intermediate therefor |
| NO784350L (no) * | 1977-12-30 | 1979-07-03 | Crc Ricerca Chim | Fremgangsmaate til alkylering av 4(5)-merkaptometyl-imidazoler med aziridinderivater |
| ZA792608B (en) * | 1978-05-30 | 1980-06-25 | Smith Kline French Lab | Nitro compounds |
| FI811376L (fi) * | 1980-05-13 | 1981-11-14 | Crc Ricerca Chim | Foerfarande foer framstaellning av n-/2-///5-(dialkylamino)-metyl-2-furanyl/-metyl/-tio/etyl/-n'-alkyl-2-nitro-1,1-etendiaminer och deras mellanprodukter |
-
1981
- 1981-01-07 PT PT7232081A patent/PT72320B/pt unknown
- 1981-01-08 CH CH8681A patent/CH650257A5/fr not_active IP Right Cessation
- 1981-01-08 FR FR8100206A patent/FR2473044A1/fr active Granted
- 1981-01-08 ES ES498389A patent/ES498389A0/es active Granted
- 1981-01-08 AR AR28390081A patent/AR225940A1/es active
- 1981-01-08 DK DK7181A patent/DK157865C/da not_active IP Right Cessation
- 1981-01-08 NL NL8100068A patent/NL8100068A/nl active Search and Examination
- 1981-01-08 YU YU2781A patent/YU42372B/xx unknown
- 1981-01-08 FI FI810039A patent/FI80450C/fi not_active IP Right Cessation
- 1981-01-08 AT AT3781A patent/AT376966B/de not_active IP Right Cessation
- 1981-01-08 HU HU3981A patent/HU182272B/hu unknown
- 1981-01-08 SE SE8100074A patent/SE449747B/sv not_active IP Right Cessation
- 1981-01-08 DE DE19813100364 patent/DE3100364A1/de active Granted
-
1985
- 1985-06-05 SE SE8502780A patent/SE460604B/sv not_active IP Right Cessation
-
1989
- 1989-10-25 JP JP27829589A patent/JPH02167259A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ATA3781A (de) | 1984-06-15 |
| ES8200673A1 (es) | 1981-11-16 |
| JPH02167259A (ja) | 1990-06-27 |
| DK157865B (da) | 1990-02-26 |
| DE3100364C2 (en, 2012) | 1989-12-28 |
| YU42372B (en) | 1988-08-31 |
| SE8100074L (sv) | 1981-07-09 |
| FI80450B (fi) | 1990-02-28 |
| YU2781A (en) | 1983-06-30 |
| DE3100364A1 (de) | 1981-11-19 |
| PT72320A (en) | 1981-02-01 |
| FR2473044B1 (en, 2012) | 1984-04-13 |
| AT376966B (de) | 1985-01-25 |
| SE8502780D0 (sv) | 1985-06-05 |
| FI810039L (fi) | 1981-07-09 |
| HU182272B (en) | 1983-12-28 |
| SE460604B (sv) | 1989-10-30 |
| AR225940A1 (es) | 1982-05-14 |
| JPH0346465B2 (en, 2012) | 1991-07-16 |
| PT72320B (en) | 1982-07-23 |
| DK7181A (da) | 1981-07-09 |
| FI80450C (fi) | 1990-06-11 |
| ES498389A0 (es) | 1981-11-16 |
| DK157865C (da) | 1990-07-30 |
| CH650257A5 (fr) | 1985-07-15 |
| SE8502780L (sv) | 1985-06-05 |
| FR2473044A1 (fr) | 1981-07-10 |
| NL8100068A (nl) | 1981-08-03 |
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