NO131675B - - Google Patents
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- Publication number
- NO131675B NO131675B NO142270A NO142270A NO131675B NO 131675 B NO131675 B NO 131675B NO 142270 A NO142270 A NO 142270A NO 142270 A NO142270 A NO 142270A NO 131675 B NO131675 B NO 131675B
- Authority
- NO
- Norway
- Prior art keywords
- molecular weight
- low molecular
- hydroxy
- mol
- thienyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- -1 thienyl metal compound Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- SNHOZPMHMQQMNI-UHFFFAOYSA-N lithium;2h-thiophen-2-ide Chemical compound [Li+].C=1C=[C-]SC=1 SNHOZPMHMQQMNI-UHFFFAOYSA-N 0.000 claims description 3
- 150000007514 bases Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 18
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229910052749 magnesium Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 238000003776 cleavage reaction Methods 0.000 description 5
- 150000003840 hydrochlorides Chemical class 0.000 description 5
- 229960000395 phenylpropanolamine Drugs 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- 230000001490 effect on brain Effects 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- RNIDWJDZNNVFDY-UHFFFAOYSA-N 3-Acetylthiophene Chemical compound CC(=O)C=1C=CSC=1 RNIDWJDZNNVFDY-UHFFFAOYSA-N 0.000 description 3
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003788 cerebral perfusion Effects 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 231100001231 less toxic Toxicity 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical group C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- ACDLOOGOFKSUPO-UHFFFAOYSA-N 2-bromo-5-methylthiophene Chemical compound CC1=CC=C(Br)S1 ACDLOOGOFKSUPO-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001233242 Lontra Species 0.000 description 1
- OEJCCWIXUKNQRW-UHFFFAOYSA-N [Li]C=1C=CSC=1 Chemical compound [Li]C=1C=CSC=1 OEJCCWIXUKNQRW-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003727 cerebral blood flow Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- 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
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691921453 DE1921453C3 (de) | 1969-04-26 | 1969-04-26 | Basische Dithienylderivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO131675B true NO131675B (de) | 1975-04-01 |
| NO131675C NO131675C (de) | 1975-07-09 |
Family
ID=5732538
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO142270A NO131675C (de) | 1969-04-26 | 1970-04-15 | |
| NO742863A NO132593C (de) | 1969-04-26 | 1974-08-08 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO742863A NO132593C (de) | 1969-04-26 | 1974-08-08 |
Country Status (16)
| Country | Link |
|---|---|
| AT (2) | AT303716B (de) |
| BE (1) | BE749296A (de) |
| CH (1) | CH539645A (de) |
| DE (1) | DE1921453C3 (de) |
| DK (1) | DK126001B (de) |
| EG (1) | EG10650A (de) |
| ES (2) | ES377719A1 (de) |
| FI (1) | FI50125C (de) |
| FR (1) | FR2042377B1 (de) |
| GB (1) | GB1296112A (de) |
| IT (1) | IT1043819B (de) |
| NL (1) | NL149174B (de) |
| NO (2) | NO131675C (de) |
| SE (1) | SE369305B (de) |
| SU (1) | SU457221A3 (de) |
| TR (1) | TR17649A (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE394280B (sv) * | 1970-04-17 | 1977-06-20 | Degussa | Forfarande for framstellning av basiskt substituerade ditienylderivat |
| JPS5033063B1 (de) * | 1971-01-19 | 1975-10-27 | ||
| GB1579541A (en) * | 1977-01-12 | 1980-11-19 | Degussa | Process for the production of (1,1 - dithien - (3)-yl - 1 - hydroxy - (3) - propyl) - (1-phenyl - 1 - hydroxy - (2) - propyl)-amine and (1,1 - dithien - (3) - yl-(1) - propen - (3) - yl) - (1 - phenyl-1 - hydroxy - (2) - propyl)- amine |
| GB1597591A (en) * | 1977-01-12 | 1981-09-09 | Degussa | Dithienyl alkylamines and alkenylamines and a process for their production |
| US4278687A (en) | 1980-01-31 | 1981-07-14 | Shell Oil Company | Inhibition of biosynthesis of triglycerides by certain N-β-phenethyl-N-thienylalkylamines |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2561899A (en) * | 1948-02-25 | 1951-07-24 | Burroughs Wellcome Co | Dithienyl allyl amines |
| DE874914C (de) * | 1950-04-28 | 1953-04-27 | Wellcome Found | Verfahren zur Herstellung von Thienylverbindungen |
| DE964056C (de) * | 1955-09-25 | 1957-05-16 | Basf Ag | Verfahren zur Herstellung von Thiophenderivaten |
| DE1194424B (de) * | 1961-11-10 | 1965-06-10 | Degussa | Verfahren zur Herstellung von basischen Thiophenderivaten |
| DE1199783B (de) * | 1962-11-30 | 1965-09-02 | Degussa | Verfahren zur Herstellung von basischen Thiophenderivaten |
| DE1219038B (de) * | 1962-12-08 | 1966-06-16 | Degussa | Verfahren zur Herstellung von Thiophenverbindungen |
| DE1217967B (de) * | 1962-12-08 | 1966-06-02 | Degussa | Verfahren zur Herstellung von basischen Thiophenderivaten |
| DE1217396B (de) * | 1963-07-04 | 1966-05-26 | Laboratorie Roger Bellon, Neuilly-sur-Seine (Frankreich) | Verfahren zur Herstellung von 1 - (Thienyl-21) - l-oxo-2-amino-propanen |
| AT255400B (de) * | 1965-03-22 | 1967-07-10 | Chemie Linz Ag | Verfahren zur Herstellung von neuen basischen Äthern |
| FR1462206A (fr) * | 1965-06-08 | 1966-04-15 | Innothera Lab Sa | Composés gem-bithiényliques et leur préparation |
-
1969
- 1969-04-26 DE DE19691921453 patent/DE1921453C3/de not_active Expired
-
1970
- 1970-03-11 CH CH359770A patent/CH539645A/de not_active IP Right Cessation
- 1970-03-20 FI FI80070A patent/FI50125C/fi active
- 1970-03-20 ES ES377719A patent/ES377719A1/es not_active Expired
- 1970-03-26 NL NL7004410A patent/NL149174B/xx not_active IP Right Cessation
- 1970-04-15 NO NO142270A patent/NO131675C/no unknown
- 1970-04-17 SU SU1437303A patent/SU457221A3/ru active
- 1970-04-17 GB GB1296112D patent/GB1296112A/en not_active Expired
- 1970-04-21 BE BE749296D patent/BE749296A/xx not_active IP Right Cessation
- 1970-04-21 TR TR1764970A patent/TR17649A/xx unknown
- 1970-04-23 DK DK210370A patent/DK126001B/da not_active IP Right Cessation
- 1970-04-24 SE SE571370A patent/SE369305B/xx unknown
- 1970-04-24 AT AT377570A patent/AT303716B/de not_active IP Right Cessation
- 1970-04-24 AT AT293571A patent/AT307399B/de not_active IP Right Cessation
- 1970-04-24 FR FR7015055A patent/FR2042377B1/fr not_active Expired
- 1970-04-24 IT IT5026170A patent/IT1043819B/it active
-
1971
- 1971-07-17 EG EG31571A patent/EG10650A/xx active
-
1972
- 1972-01-11 ES ES398738A patent/ES398738A1/es not_active Expired
-
1974
- 1974-08-08 NO NO742863A patent/NO132593C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1921453C3 (de) | 1973-04-19 |
| DK126001B (da) | 1973-05-28 |
| NL7004410A (de) | 1970-10-28 |
| ES377719A1 (es) | 1972-10-16 |
| NO132593B (de) | 1975-08-25 |
| BE749296A (fr) | 1970-10-01 |
| NO131675C (de) | 1975-07-09 |
| IT1043819B (it) | 1980-02-29 |
| SE369305B (de) | 1974-08-19 |
| ES398738A1 (es) | 1974-08-16 |
| DE1921453B2 (de) | 1972-09-28 |
| AT307399B (de) | 1973-05-25 |
| FR2042377A1 (de) | 1971-02-12 |
| GB1296112A (de) | 1972-11-15 |
| CH539645A (de) | 1973-07-31 |
| DE1921453A1 (de) | 1970-11-12 |
| AT303716B (de) | 1972-12-11 |
| TR17649A (tr) | 1975-07-23 |
| FI50125B (de) | 1975-09-01 |
| NO132593C (de) | 1975-12-03 |
| EG10650A (en) | 1976-03-31 |
| SU457221A3 (ru) | 1975-01-15 |
| FR2042377B1 (de) | 1974-02-01 |
| FI50125C (fi) | 1975-12-10 |
| NL149174B (nl) | 1976-04-15 |
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