SU419022A3 - - Google Patents
Info
- Publication number
- SU419022A3 SU419022A3 SU1688520A SU1688520A SU419022A3 SU 419022 A3 SU419022 A3 SU 419022A3 SU 1688520 A SU1688520 A SU 1688520A SU 1688520 A SU1688520 A SU 1688520A SU 419022 A3 SU419022 A3 SU 419022A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- mmol
- tetrahydrodibenzofuran
- yloxy
- tetrahydrodibenzothiophen
- Prior art date
Links
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- -1 6,7,8,9-tetrahydrodibenzofuran-2-yloxy Chemical group 0.000 description 5
- 159000000007 calcium salts Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RJPHJNSOVWUNLF-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)octanoic acid Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)CCCCCC RJPHJNSOVWUNLF-UHFFFAOYSA-N 0.000 description 2
- ZNLGDZWIVKXSBA-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzothiophen-2-yloxy)octanoic acid Chemical compound C1=C(C=CC=2SC3=C(C21)CCCC3)OC(C(=O)O)CCCCCC ZNLGDZWIVKXSBA-UHFFFAOYSA-N 0.000 description 2
- AOIBRDYGMJIGRN-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzothiophen-3-yloxy)octanoic acid Chemical compound C1=CC(=CC=2SC3=C(C21)CCCC3)OC(C(=O)O)CCCCCC AOIBRDYGMJIGRN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FTHYCAZEMLBXOJ-UHFFFAOYSA-N 2-(6,7,8,9-tetrahydrodibenzofuran-2-yloxy)propanoic acid Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)C FTHYCAZEMLBXOJ-UHFFFAOYSA-N 0.000 description 1
- VHCPLBNNFPYAFS-UHFFFAOYSA-N 2-decyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfanyl)propanedioic acid Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)SC(C(=O)O)(C(=O)O)CCCCCCCCCC VHCPLBNNFPYAFS-UHFFFAOYSA-N 0.000 description 1
- GLLSZVCKUJMZJS-UHFFFAOYSA-N 2-hexyl-2-(6,7,8,9-tetrahydrodibenzofuran-3-ylsulfanyl)propanedioic acid Chemical compound C1=CC(=CC=2OC3=C(C21)CCCC3)SC(C(=O)O)(C(=O)O)CCCCCC GLLSZVCKUJMZJS-UHFFFAOYSA-N 0.000 description 1
- AGHKGTALSVPVFI-UHFFFAOYSA-N 2-hexyl-2-(6,7,8,9-tetrahydrodibenzothiophen-2-yloxy)propanedioic acid Chemical compound C1=C(C=CC=2SC3=C(C21)CCCC3)OC(C(=O)O)(C(=O)O)CCCCCC AGHKGTALSVPVFI-UHFFFAOYSA-N 0.000 description 1
- NRJVMJLEFIUTIG-UHFFFAOYSA-N 2-hexyl-2-(6,7,8,9-tetrahydrodibenzothiophen-3-yloxy)propanedioic acid Chemical compound C1=CC(=CC=2SC3=C(C21)CCCC3)OC(C(=O)O)(C(=O)O)CCCCCC NRJVMJLEFIUTIG-UHFFFAOYSA-N 0.000 description 1
- QCCWABJHNDRSNX-UHFFFAOYSA-N 2-hexyl-2-(6,7,8,9-tetrahydrodibenzothiophen-3-ylsulfanyl)propanedioic acid Chemical compound C1=CC(=CC=2SC3=C(C21)CCCC3)SC(C(=O)O)(C(=O)O)CCCCCC QCCWABJHNDRSNX-UHFFFAOYSA-N 0.000 description 1
- PYQIJFIYVUNARD-UHFFFAOYSA-N C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)(C(=O)O)CCCCCCCCCCCCCC Chemical compound C1=C(C=CC=2OC3=C(C21)CCCC3)OC(C(=O)O)(C(=O)O)CCCCCCCCCCCCCC PYQIJFIYVUNARD-UHFFFAOYSA-N 0.000 description 1
- UEXYCVHBSCIEHR-UHFFFAOYSA-N CCCCCC(C)OC1=CC2=C(C=C1)OC3=C2CCCC3 Chemical compound CCCCCC(C)OC1=CC2=C(C=C1)OC3=C2CCCC3 UEXYCVHBSCIEHR-UHFFFAOYSA-N 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000008096 xylene 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
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
- H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L24/02—Bonding areas ; Manufacturing methods related thereto
- H01L24/04—Structure, shape, material or disposition of the bonding areas prior to the connecting process
- H01L24/05—Structure, shape, material or disposition of the bonding areas prior to the connecting process of an individual bonding area
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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 |
|---|---|---|---|
| CH425670A CH531501A (de) | 1970-03-20 | 1970-03-20 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren, ihren Salzen und funktionellen Derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU419022A3 true SU419022A3 (enrdf_load_stackoverflow) | 1974-03-05 |
Family
ID=4272721
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU711631737D SU404258A3 (enrdf_load_stackoverflow) | 1970-03-20 | 1971-03-19 | |
| SU1705729A SU390716A3 (enrdf_load_stackoverflow) | 1970-03-20 | 1971-03-19 | |
| SU1688520A SU419022A3 (enrdf_load_stackoverflow) | 1970-03-20 | 1971-03-19 | |
| SU1701191A SU391776A3 (enrdf_load_stackoverflow) | 1970-03-20 | 1971-03-19 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU711631737D SU404258A3 (enrdf_load_stackoverflow) | 1970-03-20 | 1971-03-19 | |
| SU1705729A SU390716A3 (enrdf_load_stackoverflow) | 1970-03-20 | 1971-03-19 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1701191A SU391776A3 (enrdf_load_stackoverflow) | 1970-03-20 | 1971-03-19 |
Country Status (19)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE789072A (fr) * | 1971-09-23 | 1973-03-21 | Astra Laekemedel Ab | Composes abaissant le taux de lipides du serum et leur obtention |
| US3953601A (en) * | 1973-03-16 | 1976-04-27 | Aktiebolaget Astra | Dibenzothiophene derivatives as serum lipid lowering agents |
| US4101668A (en) * | 1977-05-10 | 1978-07-18 | Bristol-Myers Company | Antiosteoporotic agents |
| US4185108A (en) * | 1977-05-10 | 1980-01-22 | Westwood Pharmaceuticals Inc. | Antiosteoporotic agents |
| US4436748A (en) * | 1980-10-20 | 1984-03-13 | Hoechst-Roussel Pharmaceuticals Inc. | Benzo[b]thiophenes |
| US4537976A (en) * | 1981-04-22 | 1985-08-27 | Hoechst-Roussel Pharmaceuticals Inc. | Benzo[b]thiophenes |
| US4528399A (en) * | 1981-04-22 | 1985-07-09 | Hoechst-Roussel Pharmaceuticals Inc. | Benzo[b]thiophenes intermediates |
| WO2000006561A1 (en) * | 1998-07-30 | 2000-02-10 | Warner-Lambert Company | Tricyclic sulfonamides and their derivatives as inhibitors of matrix metalloproteinases |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1997744A (en) * | 1932-10-05 | 1935-04-16 | Gen Aniline Works Inc | Hydroxydiphenylene compound |
-
1970
- 1970-03-20 CH CH1223972A patent/CH530388A/de not_active IP Right Cessation
- 1970-03-20 CH CH1224072A patent/CH530389A/de not_active IP Right Cessation
- 1970-03-20 CH CH425670A patent/CH531501A/de not_active IP Right Cessation
- 1970-03-20 CH CH1223872A patent/CH542837A/de not_active IP Right Cessation
- 1970-03-20 CH CH1223772A patent/CH542836A/de not_active IP Right Cessation
- 1970-03-20 CH CH1223672A patent/CH542835A/de not_active IP Right Cessation
- 1970-03-20 CH CH1224172A patent/CH531502A/de not_active IP Right Cessation
-
1971
- 1971-03-12 NO NO956/71A patent/NO134655C/no unknown
- 1971-03-12 NL NL7103358A patent/NL7103358A/xx unknown
- 1971-03-12 SE SE7103195A patent/SE378106B/xx unknown
- 1971-03-12 DK DK118371AA patent/DK128003B/da unknown
- 1971-03-18 OA OA54203A patent/OA03697A/xx unknown
- 1971-03-18 US US00125823A patent/US3784602A/en not_active Expired - Lifetime
- 1971-03-18 ES ES389360A patent/ES389360A1/es not_active Expired
- 1971-03-19 SU SU711631737D patent/SU404258A3/ru active
- 1971-03-19 AT AT239671A patent/AT302288B/de active
- 1971-03-19 AT AT965271A patent/AT307409B/de not_active IP Right Cessation
- 1971-03-19 DE DE19712113455 patent/DE2113455A1/de active Pending
- 1971-03-19 SU SU1705729A patent/SU390716A3/ru active
- 1971-03-19 SU SU1688520A patent/SU419022A3/ru active
- 1971-03-19 BE BE764536A patent/BE764536A/xx unknown
- 1971-03-19 AT AT964971A patent/AT307406B/de not_active IP Right Cessation
- 1971-03-19 AT AT964571A patent/AT307402B/de not_active IP Right Cessation
- 1971-03-19 AT AT964671A patent/AT307403B/de not_active IP Right Cessation
- 1971-03-19 IL IL36447A patent/IL36447A/en unknown
- 1971-03-19 AT AT965171A patent/AT307408B/de not_active IP Right Cessation
- 1971-03-19 FR FR7109724A patent/FR2085725B1/fr not_active Expired
- 1971-03-19 IE IE348/71A patent/IE35027B1/xx unknown
- 1971-03-19 CA CA108,184A patent/CA948209A/en not_active Expired
- 1971-03-19 AT AT964771A patent/AT307404B/de not_active IP Right Cessation
- 1971-03-19 ZA ZA711800A patent/ZA711800B/xx unknown
- 1971-03-19 AT AT964871A patent/AT307405B/de not_active IP Right Cessation
- 1971-03-19 SU SU1701191A patent/SU391776A3/ru active
- 1971-03-19 AT AT965071A patent/AT307407B/de not_active IP Right Cessation
- 1971-04-19 GB GB2467171*#A patent/GB1331839A/en not_active Expired
-
1972
- 1972-02-01 AR AR240319A patent/AR195372A1/es active
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