FI80450C - Foerfarande foer framstaellning av n-/2-//5-/(dimetylamino)metyl/-2-furanylmetyl/-tio/etyl/-n'metyl-2- nitro-1,1-etendiamin. - Google Patents
Foerfarande foer framstaellning av n-/2-//5-/(dimetylamino)metyl/-2-furanylmetyl/-tio/etyl/-n'metyl-2- nitro-1,1-etendiamin. Download PDFInfo
- Publication number
- FI80450C FI80450C FI810039A FI810039A FI80450C FI 80450 C FI80450 C FI 80450C FI 810039 A FI810039 A FI 810039A FI 810039 A FI810039 A FI 810039A FI 80450 C FI80450 C FI 80450C
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- formula
- dimethylamino
- nitro
- thio
- Prior art date
Links
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical compound CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- -1 nitromethylene Chemical group 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 9
- 229960000620 ranitidine Drugs 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000002240 furans Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 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 2
- 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 2
- BQRQOLQFLNSWNV-UHFFFAOYSA-N [5-[(dimethylamino)methyl]furan-2-yl]methanol Chemical compound CN(C)CC1=CC=C(CO)O1 BQRQOLQFLNSWNV-UHFFFAOYSA-N 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229960001380 cimetidine Drugs 0.000 description 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 2
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 239000004296 sodium metabisulphite Substances 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- BKPFPICPGCKKAA-UHFFFAOYSA-N 1-(aziridin-1-yl)-n-methyl-2-nitroethenamine Chemical compound [O-][N+](=O)C=C(NC)N1CC1 BKPFPICPGCKKAA-UHFFFAOYSA-N 0.000 description 1
- LARJDTRRRDBHNV-UHFFFAOYSA-N 1-n'-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-1-n-methyl-2-nitroethane-1,1-diamine Chemical compound [O-][N+](=O)CC(NC)NCCSCC1=CC=C(CN(C)C)O1 LARJDTRRRDBHNV-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- ZFFTZDQKIXPDAF-UHFFFAOYSA-N 2-Furanmethanethiol Chemical compound SCC1=CC=CO1 ZFFTZDQKIXPDAF-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-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
- QQDDYTLASJQRAF-UHFFFAOYSA-N CN(C)C1=COC(=C1OC)CS Chemical compound CN(C)C1=COC(=C1OC)CS QQDDYTLASJQRAF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GKMLIOQIPCDJKV-UHFFFAOYSA-N [3-[(dimethylamino)methyl]furan-2-yl]methanethiol Chemical compound CN(C)CC1=C(OC=C1)CS GKMLIOQIPCDJKV-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 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
- 239000012223 aqueous fraction Substances 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- 239000002585 base Substances 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
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 125000003916 ethylene diamine group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract 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
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI894014A FI84059C (fi) | 1980-01-08 | 1989-08-28 | Foerfarande foer framstaellning av n-/2-//5-/(dimetylamino)metyl/-2-furanylmetyl/tio/etyl/-n'-metyl-2- nitro-1,1-etendiamin. |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8000580 | 1980-01-08 | ||
| GB8000580 | 1980-01-08 | ||
| GB8000581 | 1980-01-08 | ||
| GB8000581 | 1980-01-08 | ||
| GB8039336 | 1980-12-08 | ||
| GB8039336 | 1980-12-08 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI810039L FI810039L (fi) | 1981-07-09 |
| FI80450B FI80450B (fi) | 1990-02-28 |
| FI80450C true FI80450C (fi) | 1990-06-11 |
Family
ID=27260837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI810039A FI80450C (fi) | 1980-01-08 | 1981-01-08 | Foerfarande foer framstaellning av n-/2-//5-/(dimetylamino)metyl/-2-furanylmetyl/-tio/etyl/-n'metyl-2- nitro-1,1-etendiamin. |
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 |
| SE449747B (sv) | 1987-05-18 |
| 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 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3283003A (en) | 2-(n-lower alkyl-n-cycloheptyl- and cyclooctylamino) ethyl guanidines | |
| EP0164040A2 (en) | Furan derivatives having anti-ulcer activity | |
| FI80450C (fi) | Foerfarande foer framstaellning av n-/2-//5-/(dimetylamino)metyl/-2-furanylmetyl/-tio/etyl/-n'metyl-2- nitro-1,1-etendiamin. | |
| US4968808A (en) | Process for the preparation of nitroethene derivatives | |
| KR840002007B1 (ko) | 푸란유도체의 제조방법 | |
| CZ288652B6 (cs) | Způsob přípravy derivátů kyseliny gama-merkaptokarboxylové | |
| FI76080C (fi) | Foerfarande foer framstaellning av furanderivat. | |
| US4440938A (en) | Process for the preparation of a furan derivative | |
| FI81571C (fi) | Foerfarande foer framstaellning av n-/2-//5-/(dimetylamino)-metyl/-2-furanylmetyl/tio/-etyl/-n'-metyl- 2-nitro-1,1-etendiamin. | |
| FI84060C (fi) | Foerfarande foer framstaellning av n-/2-//5-/(dimetylamino)metyl/-2-furanylmetyl/tio/etyl/-n'-metyl-2- nitro-1,1-etendiamin. | |
| AU728090B2 (en) | Intermediates for the preparation of 2-imidazoline-5-ones | |
| FI63753C (fi) | Foerfarande foer framstaellning av kristallint simetidin. | |
| FI82241B (fi) | Foerfarande foer framstaellning av n-/2-//5-/(dimetylamino)metyl/-2-furanylmetyl/tio/etyl/-n'-metyl -2-nitro-1,1-etendiamin. | |
| EP0299034B1 (en) | Process for the preparation of compounds with antiulcer action | |
| US5932584A (en) | Optically active 2,3-dihydroimidazo(1,2-C) quinazoline derivatives, the preparation and antihypertensive use thereof | |
| US4413135A (en) | Intermediates in the preparation of ranitidine | |
| FI84059B (fi) | Foerfarande foer framstaellning av n-/2-//5-/(dimetylamino)metyl/-2-furanylmetyl/tio/etyl/-n'-metyl-2- nitro-1,1-etendiamin. | |
| KR840002002B1 (ko) | 아지리딘 유도체의 제조방법 | |
| FI80687B (fi) | 2-///5-(dimetylamino)metyl-2- furanyl/metyl/tio/etanamin. | |
| JPS642590B2 (en, 2012) | ||
| CS233160B1 (cs) | Způsob výroby meziproduktů H^-antihistaminik |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |
Owner name: GLAXO GROUP LIMITED |