LU84340A1 - N-(2-(((5-(dimethylamino)-methyl-2-furanyl)-methyl)-thio)-ethyl)-n'-(3,4-methylenedioxy-benzyl)-2-nitro-1,1-ethenediamine,son procede de preparation et son application en therapeutique - Google Patents
N-(2-(((5-(dimethylamino)-methyl-2-furanyl)-methyl)-thio)-ethyl)-n'-(3,4-methylenedioxy-benzyl)-2-nitro-1,1-ethenediamine,son procede de preparation et son application en therapeutique Download PDFInfo
- Publication number
- LU84340A1 LU84340A1 LU84340A LU84340A LU84340A1 LU 84340 A1 LU84340 A1 LU 84340A1 LU 84340 A LU84340 A LU 84340A LU 84340 A LU84340 A LU 84340A LU 84340 A1 LU84340 A1 LU 84340A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- methyl
- formula
- nitro
- furanyl
- thio
- Prior art date
Links
- -1 2 - ((((5- (DIMETHYLAMINO) -METHYL-2-FURANYL) -METHYL) -THIO) -ETHYL) -N '- (3,4-METHYLENEDIOXY-BENZYL) -2-NITRO-1,1 -ETHENEDIAMINE Chemical compound 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims 2
- 239000003814 drug Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 5
- 230000000026 anti-ulcerogenic effect Effects 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- PXZIBUPXCUYYJL-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-1-methylsulfanyl-2-nitroethenamine Chemical compound [O-][N+](=O)C=C(SC)NCC1=CC=C2OCOC2=C1 PXZIBUPXCUYYJL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- JFGCGQJHMUYGLU-UHFFFAOYSA-N 2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethanamine Chemical compound CN(C)CC1=CC=C(CSCCN)O1 JFGCGQJHMUYGLU-UHFFFAOYSA-N 0.000 claims 1
- 235000014066 European mistletoe Nutrition 0.000 claims 1
- 235000012300 Rhipsalis cassutha Nutrition 0.000 claims 1
- 241000221012 Viscum Species 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 229960000620 ranitidine Drugs 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002178 gastroprotective effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 230000000767 anti-ulcer Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 description 1
- BCGUHJNLFQEPDK-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-2-nitroprop-1-ene-1,1-diamine Chemical compound NC(N)=C(CC1=CC2=C(OCO2)C=C1)[N+]([O-])=O BCGUHJNLFQEPDK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 240000007673 Origanum vulgare Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 241001433070 Xiphoides Species 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960001380 cimetidine Drugs 0.000 description 1
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 210000002417 xiphoid bone Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P35/00—Antineoplastic agents
-
- 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
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2354681 | 1981-08-18 | ||
| IT23546/81A IT1168163B (it) | 1981-08-18 | 1981-08-18 | Composto ad attivita' antiulcera, procedimento per la sua preparazione e composizioni farmaceutiche relative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU84340A1 true LU84340A1 (fr) | 1983-02-28 |
Family
ID=11208027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU84340A LU84340A1 (fr) | 1981-08-18 | 1982-08-18 | N-(2-(((5-(dimethylamino)-methyl-2-furanyl)-methyl)-thio)-ethyl)-n'-(3,4-methylenedioxy-benzyl)-2-nitro-1,1-ethenediamine,son procede de preparation et son application en therapeutique |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4431664A (en:Method) |
| JP (1) | JPS5859982A (en:Method) |
| KR (1) | KR860000851B1 (en:Method) |
| AR (1) | AR230444A1 (en:Method) |
| AT (1) | AT383597B (en:Method) |
| AU (1) | AU533719B2 (en:Method) |
| BE (1) | BE894093A (en:Method) |
| CA (1) | CA1182121A (en:Method) |
| CH (1) | CH650259A5 (en:Method) |
| DE (1) | DE3230265C2 (en:Method) |
| DK (1) | DK156067C (en:Method) |
| ES (1) | ES8306372A1 (en:Method) |
| FR (1) | FR2511675A1 (en:Method) |
| GB (1) | GB2104071B (en:Method) |
| GR (1) | GR76260B (en:Method) |
| IT (1) | IT1168163B (en:Method) |
| LU (1) | LU84340A1 (en:Method) |
| NL (1) | NL186447C (en:Method) |
| NO (1) | NO159448C (en:Method) |
| PH (1) | PH19228A (en:Method) |
| PT (1) | PT75440B (en:Method) |
| SE (1) | SE448456B (en:Method) |
| ZA (1) | ZA825718B (en:Method) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1175808B (it) * | 1984-03-07 | 1987-07-15 | Ausonia Farma Srl | Procedimento per la preparazione di composto con attivita' antiulcera |
| IT1196133B (it) * | 1984-06-06 | 1988-11-10 | Ausonia Farma Srl | Derivati furanici con attivita' antiulcera |
| EP0269650A1 (en) * | 1986-03-28 | 1988-06-08 | Recordati Farma Srl | Synthesis of antiulcer compounds |
| GB8907700D0 (en) * | 1989-04-05 | 1989-05-17 | Fine Organics Ltd | Preparation of substituted ethenes |
| JPH0416036U (en:Method) * | 1990-05-31 | 1992-02-10 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4140681A (en) * | 1974-11-08 | 1979-02-20 | Mitsubishi Chemical Industries, Limited | N2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US4233302A (en) * | 1977-12-23 | 1980-11-11 | Glaxo Group Limited | Amine derivatives and pharmaceutical compositions containing them |
-
1981
- 1981-08-18 IT IT23546/81A patent/IT1168163B/it active
-
1982
- 1982-07-30 CH CH4612/82A patent/CH650259A5/it not_active IP Right Cessation
- 1982-08-04 AU AU86731/82A patent/AU533719B2/en not_active Ceased
- 1982-08-05 US US06/405,332 patent/US4431664A/en not_active Expired - Fee Related
- 1982-08-06 ZA ZA825718A patent/ZA825718B/xx unknown
- 1982-08-09 DK DK357182A patent/DK156067C/da not_active IP Right Cessation
- 1982-08-11 NL NLAANVRAGE8203160,A patent/NL186447C/xx not_active IP Right Cessation
- 1982-08-12 BE BE2/59796A patent/BE894093A/nl not_active IP Right Cessation
- 1982-08-12 CA CA000409313A patent/CA1182121A/en not_active Expired
- 1982-08-12 SE SE8204670A patent/SE448456B/sv not_active IP Right Cessation
- 1982-08-13 JP JP57141602A patent/JPS5859982A/ja active Granted
- 1982-08-13 FR FR8214079A patent/FR2511675A1/fr active Granted
- 1982-08-13 GR GR69044A patent/GR76260B/el unknown
- 1982-08-13 PH PH27729A patent/PH19228A/en unknown
- 1982-08-13 GB GB08223316A patent/GB2104071B/en not_active Expired
- 1982-08-14 DE DE3230265A patent/DE3230265C2/de not_active Expired
- 1982-08-17 KR KR8203689A patent/KR860000851B1/ko not_active Expired
- 1982-08-17 NO NO822801A patent/NO159448C/no unknown
- 1982-08-17 ES ES515068A patent/ES8306372A1/es not_active Expired
- 1982-08-17 AT AT0312282A patent/AT383597B/de not_active IP Right Cessation
- 1982-08-18 AR AR290336A patent/AR230444A1/es active
- 1982-08-18 PT PT75440A patent/PT75440B/pt not_active IP Right Cessation
- 1982-08-18 LU LU84340A patent/LU84340A1/fr unknown
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