NO132836B - - Google Patents
Info
- Publication number
- NO132836B NO132836B NO142671A NO142671A NO132836B NO 132836 B NO132836 B NO 132836B NO 142671 A NO142671 A NO 142671A NO 142671 A NO142671 A NO 142671A NO 132836 B NO132836 B NO 132836B
- Authority
- NO
- Norway
- Prior art keywords
- thieno
- general formula
- mixture
- hours
- water
- Prior art date
Links
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003551 thiepines Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 11
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- -1 bis-bromomethyl compounds Chemical class 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 6
- NIGNBCLEMMGDQP-UHFFFAOYSA-N 1-benzothiepine Chemical compound S1C=CC=CC2=CC=CC=C12 NIGNBCLEMMGDQP-UHFFFAOYSA-N 0.000 description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- IAMFYFXLDSBTGG-UHFFFAOYSA-N 5h-1-benzothiepin-4-one Chemical compound S1C=CC(=O)CC2=CC=CC=C21 IAMFYFXLDSBTGG-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229960002317 succinimide Drugs 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- XJDDOXBKJTWRQN-UHFFFAOYSA-N 4,5-bis(bromomethyl)thieno[2,3-b][1]benzothiepine Chemical compound BrCC1=C(CBr)C2=CC=CC=C2SC2=C1C=CS2 XJDDOXBKJTWRQN-UHFFFAOYSA-N 0.000 description 1
- ASUNAYOVHNVKFK-UHFFFAOYSA-N 5-methyl-5h-thieno[2,3-b][1]benzothiepin-4-one Chemical compound O=C1C(C)C2=CC=CC=C2SC2=C1C=CS2 ASUNAYOVHNVKFK-UHFFFAOYSA-N 0.000 description 1
- NHQMMNSYWQXOFN-UHFFFAOYSA-N C(CCC)N1CC2=C(C1)C1=C(SC3=C2SC=C3)C=CC=C1 Chemical compound C(CCC)N1CC2=C(C1)C1=C(SC3=C2SC=C3)C=CC=C1 NHQMMNSYWQXOFN-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
- 150000007513 acids Chemical class 0.000 description 1
- 230000002908 adrenolytic effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000003236 psychic effect Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000012345 traction test Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1906169A CH520699A (de) | 1969-12-23 | 1969-12-23 | Verfahren zur Herstellung von neuen Thiepinderivaten |
| CH1906269A CH518958A (de) | 1969-12-23 | 1969-12-23 | Verfahren zur Herstellung von neuen Thiepinderivaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO132836B true NO132836B (de) | 1975-10-06 |
| NO132836C NO132836C (de) | 1976-01-14 |
Family
ID=25722008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO142671A NO132836C (de) | 1969-12-23 | 1971-04-16 |
Country Status (18)
| Country | Link |
|---|---|
| JP (2) | JPS4910518B1 (de) |
| AT (3) | AT305291B (de) |
| BE (1) | BE760676A (de) |
| BG (3) | BG17808A3 (de) |
| CA (1) | CA940531A (de) |
| CS (3) | CS171703B2 (de) |
| DE (1) | DE2063178C3 (de) |
| DK (1) | DK124689B (de) |
| ES (3) | ES386715A1 (de) |
| FI (1) | FI50629C (de) |
| FR (1) | FR2081394A1 (de) |
| IE (1) | IE34832B1 (de) |
| IL (1) | IL35891A (de) |
| NL (1) | NL7018352A (de) |
| NO (1) | NO132836C (de) |
| PL (1) | PL81742B1 (de) |
| SE (1) | SE358168B (de) |
| SU (3) | SU489334A3 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5429746U (de) * | 1977-07-30 | 1979-02-27 | ||
| JPH0372491U (de) * | 1989-11-20 | 1991-07-22 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1081360A (en) * | 1965-08-25 | 1967-08-31 | Spofa Vereinigte Pharma Werke | Novel 4-substituted-4,5-dihydrothieno-(2,3-b)-benzo(f)thiepines and process for the preparation thereof |
| NL6806701A (de) * | 1967-05-19 | 1968-11-20 | ||
| SE364591B (de) * | 1968-11-19 | 1974-02-25 | Western Electric Co | |
| CH556878A (de) * | 1969-03-31 | 1974-12-13 | Takeda Chemical Industries Ltd | Verfahren zur herstellung des neuen antibiotikums b2847rb. |
-
1970
- 1970-12-16 SE SE1705070A patent/SE358168B/xx unknown
- 1970-12-16 FI FI339870A patent/FI50629C/fi active
- 1970-12-16 DK DK638670A patent/DK124689B/da unknown
- 1970-12-16 NL NL7018352A patent/NL7018352A/xx unknown
- 1970-12-22 AT AT1000071A patent/AT305291B/de not_active IP Right Cessation
- 1970-12-22 ES ES386715A patent/ES386715A1/es not_active Expired
- 1970-12-22 BG BG1776670A patent/BG17808A3/xx unknown
- 1970-12-22 AT AT1000171A patent/AT305292B/de not_active IP Right Cessation
- 1970-12-22 CS CS407270A patent/CS171703B2/cs unknown
- 1970-12-22 AT AT1153970A patent/AT302309B/de not_active IP Right Cessation
- 1970-12-22 CA CA101,249A patent/CA940531A/en not_active Expired
- 1970-12-22 CS CS407175A patent/CS171702B2/cs unknown
- 1970-12-22 IL IL3589170A patent/IL35891A/xx unknown
- 1970-12-22 ES ES386716A patent/ES386716A1/es not_active Expired
- 1970-12-22 DE DE19702063178 patent/DE2063178C3/de not_active Expired
- 1970-12-22 PL PL14516470A patent/PL81742B1/pl unknown
- 1970-12-22 BE BE760676A patent/BE760676A/xx unknown
- 1970-12-22 ES ES386714A patent/ES386714A1/es not_active Expired
- 1970-12-22 FR FR7046194A patent/FR2081394A1/fr active Granted
- 1970-12-22 BG BG1776570A patent/BG17977A3/xx unknown
- 1970-12-22 BG BG1638370A patent/BG17807A3/xx unknown
- 1970-12-22 IE IE162770A patent/IE34832B1/xx unknown
- 1970-12-22 CS CS870670A patent/CS171701B2/cs unknown
- 1970-12-23 SU SU1601468A patent/SU489334A3/ru active
- 1970-12-23 SU SU1601466A patent/SU439986A3/ru active
- 1970-12-23 SU SU1601469A patent/SU415882A3/ru active
-
1971
- 1971-04-16 NO NO142671A patent/NO132836C/no unknown
-
1972
- 1972-06-08 JP JP47056525A patent/JPS4910518B1/ja active Pending
- 1972-06-08 JP JP47056524A patent/JPS4818240B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA940531A (en) | 1974-01-22 |
| BE760676A (fr) | 1971-06-22 |
| IE34832L (en) | 1971-06-23 |
| IE34832B1 (en) | 1975-09-03 |
| NO132836C (de) | 1976-01-14 |
| PL81742B1 (en) | 1975-08-30 |
| BG17977A3 (de) | 1974-03-05 |
| BG17807A3 (de) | 1973-12-25 |
| NL7018352A (de) | 1971-06-25 |
| CS171702B2 (de) | 1976-10-29 |
| AT305292B (de) | 1973-02-26 |
| BG17808A3 (de) | 1973-12-25 |
| DE2063178B2 (de) | 1979-08-02 |
| IL35891A (en) | 1974-05-16 |
| AT305291B (de) | 1973-02-26 |
| FR2081394B1 (de) | 1974-05-24 |
| SU415882A3 (de) | 1974-02-15 |
| ES386716A1 (es) | 1974-01-16 |
| AT302309B (de) | 1972-10-10 |
| SU489334A3 (ru) | 1975-10-25 |
| DK124689B (da) | 1972-11-13 |
| ES386714A1 (es) | 1974-08-16 |
| SU439986A3 (ru) | 1974-08-15 |
| JPS4910518B1 (de) | 1974-03-11 |
| FI50629C (fi) | 1976-05-10 |
| FR2081394A1 (en) | 1971-12-03 |
| CS171701B2 (de) | 1976-10-29 |
| DE2063178C3 (de) | 1980-04-03 |
| SE358168B (de) | 1973-07-23 |
| DE2063178A1 (de) | 1971-07-01 |
| ES386715A1 (es) | 1974-01-16 |
| FI50629B (de) | 1976-02-02 |
| JPS4818240B1 (de) | 1973-06-04 |
| CS171703B2 (de) | 1976-10-29 |
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