DE2011024A1 - Patentwesen, Ost-Berlin WP138598 Verfahren zur Herstellung von neuen 3-Carbalkoxy-l-thia-isochroman-l.l-dioxid-Derivaten - Google Patents
Patentwesen, Ost-Berlin WP138598 Verfahren zur Herstellung von neuen 3-Carbalkoxy-l-thia-isochroman-l.l-dioxid-DerivatenInfo
- Publication number
- DE2011024A1 DE2011024A1 DE19702011024 DE2011024A DE2011024A1 DE 2011024 A1 DE2011024 A1 DE 2011024A1 DE 19702011024 DE19702011024 DE 19702011024 DE 2011024 A DE2011024 A DE 2011024A DE 2011024 A1 DE2011024 A1 DE 2011024A1
- Authority
- DE
- Germany
- Prior art keywords
- thia
- general formula
- dioxide
- radicals
- meaning
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- -1 alkyl radical Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000011541 reaction mixture 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- SCCDQYPEOIRVGX-UHFFFAOYSA-N Acetyleugenol Chemical compound COC1=CC(CC=C)=CC=C1OC(C)=O SCCDQYPEOIRVGX-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 241000410581 Rhipidolestes lii Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/39—Heterocyclic compounds having sulfur as a ring hetero atom having oxygen in the same ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD13859869 | 1969-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2011024A1 true DE2011024A1 (de) | 1970-09-24 |
Family
ID=5481042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702011024 Pending DE2011024A1 (de) | 1969-03-17 | 1970-03-09 | Patentwesen, Ost-Berlin WP138598 Verfahren zur Herstellung von neuen 3-Carbalkoxy-l-thia-isochroman-l.l-dioxid-Derivaten |
Country Status (12)
| Country | Link |
|---|---|
| AT (2) | AT296982B (xx) |
| BG (3) | BG18184A3 (xx) |
| CH (1) | CH530996A (xx) |
| CS (3) | CS166362B1 (xx) |
| DE (1) | DE2011024A1 (xx) |
| DK (1) | DK123722B (xx) |
| FI (1) | FI49975C (xx) |
| FR (1) | FR2034995A1 (xx) |
| PL (1) | PL79282B1 (xx) |
| RO (3) | RO57971A (xx) |
| SE (1) | SE364048B (xx) |
| SU (3) | SU493960A3 (xx) |
-
1970
- 1970-03-09 DE DE19702011024 patent/DE2011024A1/de active Pending
- 1970-03-10 AT AT158471A patent/AT296982B/de active
- 1970-03-10 AT AT225770A patent/AT295531B/de not_active IP Right Cessation
- 1970-03-13 DK DK126170A patent/DK123722B/da unknown
- 1970-03-14 PL PL13939470A patent/PL79282B1/pl unknown
- 1970-03-16 CS CS782373A patent/CS166362B1/cs unknown
- 1970-03-16 SU SU1414159A patent/SU493960A3/ru active
- 1970-03-16 SU SU1630922A patent/SU390719A3/ru active
- 1970-03-16 BG BG1852970A patent/BG18184A3/xx unknown
- 1970-03-16 FR FR7009312A patent/FR2034995A1/fr active Granted
- 1970-03-16 CS CS782470A patent/CS166363B1/cs unknown
- 1970-03-16 SU SU1749941A patent/SU413679A3/ru active
- 1970-03-16 BG BG1419870A patent/BG17563A3/xx unknown
- 1970-03-16 BG BG016813A patent/BG18183A3/xx unknown
- 1970-03-16 CS CS173170A patent/CS166361B1/cs unknown
- 1970-03-17 FI FI72470A patent/FI49975C/fi active
- 1970-03-17 RO RO6279070A patent/RO57971A/ro unknown
- 1970-03-17 RO RO7580670A patent/RO58873A/ro unknown
- 1970-03-17 RO RO7393870A patent/RO58741A/ro unknown
- 1970-03-17 CH CH401870A patent/CH530996A/de not_active IP Right Cessation
- 1970-03-17 SE SE357470A patent/SE364048B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS166361B1 (xx) | 1976-02-27 |
| FI49975B (xx) | 1975-07-31 |
| DK123722B (da) | 1972-07-24 |
| SU413679A3 (xx) | 1974-01-30 |
| RO58741A (xx) | 1975-11-15 |
| CS166363B1 (en) | 1976-02-27 |
| SE364048B (xx) | 1974-02-11 |
| AT296982B (de) | 1972-02-15 |
| AT295531B (de) | 1971-12-15 |
| RO57971A (xx) | 1975-06-15 |
| BG17563A3 (xx) | 1973-11-10 |
| SU390719A3 (xx) | 1973-07-11 |
| BG18183A3 (bg) | 1974-09-02 |
| FI49975C (fi) | 1975-11-10 |
| PL79282B1 (xx) | 1975-06-30 |
| RO58873A (xx) | 1975-10-15 |
| BG18184A3 (xx) | 1974-09-02 |
| CH530996A (de) | 1972-11-30 |
| FR2034995A1 (fr) | 1970-12-18 |
| FR2034995B1 (xx) | 1973-07-13 |
| CS166362B1 (xx) | 1976-02-27 |
| SU493960A3 (ru) | 1975-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |