FI81571C - 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
- FI81571C FI81571C FI821612A FI821612A FI81571C FI 81571 C FI81571 C FI 81571C FI 821612 A FI821612 A FI 821612A FI 821612 A FI821612 A FI 821612A FI 81571 C FI81571 C FI 81571C
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- dimethylamino
- formula
- reaction
- disulfide
- 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 6
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 12
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 11
- BQRQOLQFLNSWNV-UHFFFAOYSA-N [5-[(dimethylamino)methyl]furan-2-yl]methanol Chemical compound CN(C)CC1=CC=C(CO)O1 BQRQOLQFLNSWNV-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 claims description 5
- 229940099500 cystamine Drugs 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229940012017 ethylenediamine Drugs 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- -1 ethanol Chemical compound 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- 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 2
- CUHUMGUJAOWGIT-UHFFFAOYSA-N 1-n'-methyl-2-nitroethane-1,1-diamine Chemical compound CNC(N)C[N+]([O-])=O CUHUMGUJAOWGIT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229960000620 ranitidine Drugs 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WXEPXQSJJAEGFO-UHFFFAOYSA-N (3-methylfuran-2-yl)methanol Chemical compound CC=1C=COC=1CO WXEPXQSJJAEGFO-UHFFFAOYSA-N 0.000 description 1
- YUFRRMZSSPQMOS-UHFFFAOYSA-N 2-(2-aminoethyldisulfanyl)ethanamine;hydron;dichloride Chemical compound Cl.Cl.NCCSSCCN YUFRRMZSSPQMOS-UHFFFAOYSA-N 0.000 description 1
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8113944 | 1981-05-07 | ||
| GB8113944 | 1981-05-07 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI821612A0 FI821612A0 (fi) | 1982-05-07 |
| FI821612L FI821612L (fi) | 1982-11-08 |
| FI81571B FI81571B (fi) | 1990-07-31 |
| FI81571C true FI81571C (fi) | 1990-11-12 |
Family
ID=10521625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI821612A FI81571C (fi) | 1981-05-07 | 1982-05-07 | 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 |
|---|---|
| US (1) | US4394516A (en, 2012) |
| EP (1) | EP0064869B1 (en, 2012) |
| JP (1) | JPS57192378A (en, 2012) |
| KR (1) | KR860000100B1 (en, 2012) |
| AR (1) | AR229878A1 (en, 2012) |
| AT (1) | ATE17578T1 (en, 2012) |
| AU (1) | AU552725B2 (en, 2012) |
| CA (1) | CA1177490A (en, 2012) |
| DE (1) | DE3268639D1 (en, 2012) |
| DK (1) | DK152043C (en, 2012) |
| ES (1) | ES8307235A1 (en, 2012) |
| FI (1) | FI81571C (en, 2012) |
| PT (1) | PT74855B (en, 2012) |
| ZA (1) | ZA823170B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FI88157C (fi) * | 1983-07-15 | 1993-04-13 | Richter Gedeon Vegyeszet | Foerfarande foer framstaellning av vaetekloriden av 1- 2-/5-dimetylaminometyl-2-(furylmetyltio)-etyl/ -amino-1-metylamino-2-nitroetylen |
| DE3444156A1 (de) * | 1984-12-04 | 1986-06-05 | Xaver Fendt & Co, 8952 Marktoberdorf | Bremseinrichtung fuer anhaenger von zugmaschinen |
| JPH0725745B2 (ja) * | 1986-11-11 | 1995-03-22 | 株式会社日本触媒 | アミン化合物の製造方法 |
| IT1215344B (it) * | 1987-01-27 | 1990-02-08 | Dessy S R L Ora Recordati Farm | Procedimento per la preparazione di composti ad attivita' anti-ulcera. |
| US5672724A (en) * | 1994-12-08 | 1997-09-30 | Hoechst Marion Roussel, Inc. | Processes for preparing ranitidine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1565966A (en) * | 1976-08-04 | 1980-04-23 | Allen & Hanburys Ltd | Aminoalkyl furan derivatives |
| US4157340A (en) * | 1978-06-27 | 1979-06-05 | Bristol-Meyers Company | N,N'-[Bis(N-cyanoguanyl)]cystamine derivatives |
| CH645098A5 (de) | 1978-11-02 | 1984-09-14 | Pliva Pharm & Chem Works | Verfahren zur herstellung von n-cyan-n'-methyl-n''-(2-mercaptoaethyl)guanidin. |
-
1982
- 1982-04-21 AR AR289168A patent/AR229878A1/es active
- 1982-05-06 DK DK206582A patent/DK152043C/da not_active IP Right Cessation
- 1982-05-07 AT AT82302332T patent/ATE17578T1/de active
- 1982-05-07 PT PT74855A patent/PT74855B/pt unknown
- 1982-05-07 US US06/375,963 patent/US4394516A/en not_active Expired - Lifetime
- 1982-05-07 JP JP57076446A patent/JPS57192378A/ja active Granted
- 1982-05-07 ES ES512026A patent/ES8307235A1/es not_active Expired
- 1982-05-07 KR KR8201992A patent/KR860000100B1/ko not_active Expired
- 1982-05-07 CA CA000402508A patent/CA1177490A/en not_active Expired
- 1982-05-07 DE DE8282302332T patent/DE3268639D1/de not_active Expired
- 1982-05-07 EP EP82302332A patent/EP0064869B1/en not_active Expired
- 1982-05-07 AU AU83491/82A patent/AU552725B2/en not_active Ceased
- 1982-05-07 ZA ZA823170A patent/ZA823170B/xx unknown
- 1982-05-07 FI FI821612A patent/FI81571C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES512026A0 (es) | 1983-02-01 |
| ZA823170B (en) | 1983-03-30 |
| FI81571B (fi) | 1990-07-31 |
| ATE17578T1 (de) | 1986-02-15 |
| DK152043C (da) | 1988-07-18 |
| FI821612L (fi) | 1982-11-08 |
| DK152043B (da) | 1988-01-25 |
| CA1177490A (en) | 1984-11-06 |
| PT74855B (en) | 1985-06-28 |
| DK206582A (da) | 1982-11-08 |
| JPS57192378A (en) | 1982-11-26 |
| EP0064869A1 (en) | 1982-11-17 |
| DE3268639D1 (en) | 1986-03-06 |
| JPH033672B2 (en, 2012) | 1991-01-21 |
| KR830010092A (ko) | 1983-12-26 |
| AU8349182A (en) | 1982-11-11 |
| AR229878A1 (es) | 1983-12-30 |
| AU552725B2 (en) | 1986-06-19 |
| US4394516A (en) | 1983-07-19 |
| KR860000100B1 (ko) | 1986-02-19 |
| FI821612A0 (fi) | 1982-05-07 |
| EP0064869B1 (en) | 1986-01-22 |
| PT74855A (en) | 1982-06-01 |
| ES8307235A1 (es) | 1983-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: GLAXO GROUP LIMITED |