DE2610704C2 - 4-Hydroxymethyl-2-iodmethyl-1,3-dioxolan, Verfahren zu seiner Herstellung und diese Verbindung enthaltende Arzneimittel - Google Patents
4-Hydroxymethyl-2-iodmethyl-1,3-dioxolan, Verfahren zu seiner Herstellung und diese Verbindung enthaltende ArzneimittelInfo
- Publication number
- DE2610704C2 DE2610704C2 DE2610704A DE2610704A DE2610704C2 DE 2610704 C2 DE2610704 C2 DE 2610704C2 DE 2610704 A DE2610704 A DE 2610704A DE 2610704 A DE2610704 A DE 2610704A DE 2610704 C2 DE2610704 C2 DE 2610704C2
- Authority
- DE
- Germany
- Prior art keywords
- dioxolane
- hydroxymethyl
- compound
- iodomethyl
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 title description 12
- 239000003814 drug Substances 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- NEIPZWZQHXCYDV-UHFFFAOYSA-N domiodol Chemical compound OCC1COC(CI)O1 NEIPZWZQHXCYDV-UHFFFAOYSA-N 0.000 title 1
- XQCWOAMYQRDOQY-UHFFFAOYSA-N 2-iodoacetaldehyde Chemical compound ICC=O XQCWOAMYQRDOQY-UHFFFAOYSA-N 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
- 239000003172 expectorant agent Substances 0.000 description 2
- 230000003419 expectorant effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 150000002496 iodine Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- ZSLVLMWYSIERCN-UHFFFAOYSA-N [2-(bromomethyl)-1,3-dioxolan-4-yl]methanol Chemical compound OCC1COC(CBr)O1 ZSLVLMWYSIERCN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 229940039231 contrast media Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229940066493 expectorants Drugs 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- -1 iodomethyl Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- 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
- C07D317/10—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 not condensed with other rings
- C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- 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
- C07D317/10—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 not condensed with other rings
- C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/20—Free hydroxyl or mercaptan
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2192975A IT1037122B (it) | 1975-04-01 | 1975-04-01 | Derivati alogenati dell 1 3 dios solano ad attivita mucolitica |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2610704A1 DE2610704A1 (de) | 1976-10-14 |
| DE2610704C2 true DE2610704C2 (de) | 1985-04-11 |
Family
ID=11188946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2610704A Expired DE2610704C2 (de) | 1975-04-01 | 1976-03-13 | 4-Hydroxymethyl-2-iodmethyl-1,3-dioxolan, Verfahren zu seiner Herstellung und diese Verbindung enthaltende Arzneimittel |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4085223A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS51122065A (cg-RX-API-DMAC10.html) |
| BE (1) | BE880492Q (cg-RX-API-DMAC10.html) |
| CA (1) | CA1064044A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2610704C2 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2305979A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1487165A (cg-RX-API-DMAC10.html) |
| IT (1) | IT1037122B (cg-RX-API-DMAC10.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4861764A (en) * | 1986-11-17 | 1989-08-29 | Macro Chem. Corp. | Percutaneous absorption enhancers, compositions containing same and method of use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2589296A (en) * | 1950-06-02 | 1952-03-18 | Searle & Co | 2-trihalomethyl-1, 3-dioxolane-4-carboxybenzoate and carboxyalkanoate |
| US2872378A (en) * | 1954-05-10 | 1959-02-03 | Denver Chemical Mfg Company | Therapeutic compositions containing iodopropylideneglycerol |
| US3812261A (en) * | 1972-03-15 | 1974-05-21 | Ici America Inc | Method of producing tranquilization with dioxolanyl alcohols and their halogen derivatives |
| US3996376A (en) * | 1972-03-28 | 1976-12-07 | Ici United States Inc. | Halogenated dioxolane tranquilizers |
| ES417572A1 (es) * | 1973-08-03 | 1976-03-16 | Boehringer Mannheim Gmbh | Procedimiento para la obtencion del 2-(iodoetil)-1,3-dioxo-lano-4-metanol. |
-
1975
- 1975-04-01 IT IT2192975A patent/IT1037122B/it active
-
1976
- 1976-03-13 DE DE2610704A patent/DE2610704C2/de not_active Expired
- 1976-03-22 GB GB11467/76A patent/GB1487165A/en not_active Expired
- 1976-03-24 CA CA248,738A patent/CA1064044A/en not_active Expired
- 1976-03-24 US US05/670,174 patent/US4085223A/en not_active Expired - Lifetime
- 1976-03-31 FR FR7609398A patent/FR2305979A1/fr active Granted
- 1976-04-01 JP JP51037034A patent/JPS51122065A/ja active Pending
-
1979
- 1979-12-07 BE BE0/198474A patent/BE880492Q/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2610704A1 (de) | 1976-10-14 |
| GB1487165A (en) | 1977-09-28 |
| IT1037122B (it) | 1979-11-10 |
| JPS51122065A (en) | 1976-10-25 |
| BE880492Q (fr) | 1980-04-01 |
| CA1064044A (en) | 1979-10-09 |
| US4085223A (en) | 1978-04-18 |
| FR2305979B1 (cg-RX-API-DMAC10.html) | 1979-03-09 |
| FR2305979A1 (fr) | 1976-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |