CA1064044A - Halogenated derivatives of 1,3-dioxolane having mucolytic activity - Google Patents
Halogenated derivatives of 1,3-dioxolane having mucolytic activityInfo
- Publication number
- CA1064044A CA1064044A CA248,738A CA248738A CA1064044A CA 1064044 A CA1064044 A CA 1064044A CA 248738 A CA248738 A CA 248738A CA 1064044 A CA1064044 A CA 1064044A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- alkyl radical
- carbon atoms
- substituent
- linear
- 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
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical class C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 title claims abstract 4
- 230000000510 mucolytic effect Effects 0.000 title 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 9
- 125000001424 substituent group Chemical group 0.000 claims abstract 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract 3
- LWCIBYRXSHRIAP-UHFFFAOYSA-N 3-phenylmethoxypropane-1,2-diol Chemical compound OCC(O)COCC1=CC=CC=C1 LWCIBYRXSHRIAP-UHFFFAOYSA-N 0.000 claims abstract 2
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 claims abstract 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract 2
- 239000007859 condensation product Substances 0.000 claims abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 13
- 239000000126 substance Substances 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 125000006083 1-bromoethyl group Chemical group 0.000 claims 1
- 125000005997 bromomethyl group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- -1 iodomethyl Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000003172 expectorant agent Substances 0.000 abstract 1
- 230000003419 expectorant effect Effects 0.000 abstract 1
- 229940066493 expectorants Drugs 0.000 abstract 1
- 210000003097 mucus Anatomy 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000006810 Caesalpinia ciliata Nutrition 0.000 description 1
- 241000059739 Caesalpinia ciliata Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- 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 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- NNYBQONXHNTVIJ-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=C1C(C=CC=C1CC)=C1N2 NNYBQONXHNTVIJ-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 101150085091 lat-2 gene Proteins 0.000 description 1
- 229940063718 lodine Drugs 0.000 description 1
- RJMUSRYZPJIFPJ-UHFFFAOYSA-N niclosamide Chemical compound OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl RJMUSRYZPJIFPJ-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1064044A true CA1064044A (en) | 1979-10-09 |
Family
ID=11188946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA248,738A Expired CA1064044A (en) | 1975-04-01 | 1976-03-24 | Halogenated derivatives of 1,3-dioxolane having mucolytic activity |
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 |
| US4085223A (en) | 1978-04-18 |
| DE2610704C2 (de) | 1985-04-11 |
| FR2305979B1 (cg-RX-API-DMAC10.html) | 1979-03-09 |
| FR2305979A1 (fr) | 1976-10-29 |
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