CA1049011A - Triazolobenzocycloalkylthiadiazine derivatives - Google Patents
Triazolobenzocycloalkylthiadiazine derivativesInfo
- Publication number
- CA1049011A CA1049011A CA76246112A CA246112A CA1049011A CA 1049011 A CA1049011 A CA 1049011A CA 76246112 A CA76246112 A CA 76246112A CA 246112 A CA246112 A CA 246112A CA 1049011 A CA1049011 A CA 1049011A
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- triazolo
- thiadiazine
- dihydro
- bromo
- 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
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 41
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UXVCSPSWUNMPMT-UHFFFAOYSA-N 2-bromo-2,3-dihydroinden-1-one Chemical compound C1=CC=C2C(=O)C(Br)CC2=C1 UXVCSPSWUNMPMT-UHFFFAOYSA-N 0.000 claims description 6
- AYNCWMIFKFADCZ-UHFFFAOYSA-N 2-bromo-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2C(=O)C(Br)CCC2=C1 AYNCWMIFKFADCZ-UHFFFAOYSA-N 0.000 claims description 6
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 6
- 150000003852 triazoles Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- NAXVBXDTOCUKNH-UHFFFAOYSA-N 2-bromo-6-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1C(Br)CCC2=CC(OC)=CC=C21 NAXVBXDTOCUKNH-UHFFFAOYSA-N 0.000 claims description 2
- KLVQAIJZDCCJRZ-UHFFFAOYSA-N 2h-1,3,4-thiadiazine Chemical compound C1SC=CN=N1 KLVQAIJZDCCJRZ-UHFFFAOYSA-N 0.000 claims description 2
- DLLBXBCKFUPBJE-UHFFFAOYSA-N 4-amino-1h-1,2,4-triazole-5-thione Chemical compound NN1C=NNC1=S DLLBXBCKFUPBJE-UHFFFAOYSA-N 0.000 claims description 2
- NHJQUZUFQOQBNE-UHFFFAOYSA-N 4-amino-3-ethyl-1h-1,2,4-triazole-5-thione Chemical compound CCC1=NNC(=S)N1N NHJQUZUFQOQBNE-UHFFFAOYSA-N 0.000 claims 3
- XDBKPTOOJLUTRK-UHFFFAOYSA-N 3-ethyl-10,10a-dihydroindeno[1,2-e]-s-triazolo[3,4-b][1,3,4]thiadiazine Chemical compound C1=CC=C2C3=NN4C(CC)=NN=C4SC3CC2=C1 XDBKPTOOJLUTRK-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 230000001430 anti-depressive effect Effects 0.000 abstract description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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- -1 cyclohexyl radicals Chemical class 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
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- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
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- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000006188 syrup Substances 0.000 description 6
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- 208000009132 Catalepsy Diseases 0.000 description 5
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- 125000000753 cycloalkyl group Chemical group 0.000 description 5
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- 235000019698 starch Nutrition 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
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- 239000007864 aqueous solution Substances 0.000 description 4
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 4
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- 239000008101 lactose Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
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- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 4
- 229960003147 reserpine Drugs 0.000 description 4
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- PELQCSAKKLXVLQ-UHFFFAOYSA-N 2-bromo-4-methyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2C(C)CC(Br)C(=O)C2=C1 PELQCSAKKLXVLQ-UHFFFAOYSA-N 0.000 description 3
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
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- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
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- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical class C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
- NSPWDODUFKPVMO-UHFFFAOYSA-N 2-bromo-5,6-dimethoxy-2,3-dihydroinden-1-one Chemical compound C1=C(OC)C(OC)=CC2=C1C(=O)C(Br)C2 NSPWDODUFKPVMO-UHFFFAOYSA-N 0.000 description 2
- MHOFMGWBCRJNRX-UHFFFAOYSA-N 2-iodo-3,4-dihydro-2h-naphthalen-1-one Chemical class C1=CC=C2C(=O)C(I)CCC2=C1 MHOFMGWBCRJNRX-UHFFFAOYSA-N 0.000 description 2
- RUORWXQKVXTQJJ-UHFFFAOYSA-N 4-methyl-2,3-dihydroinden-1-one Chemical group CC1=CC=CC2=C1CCC2=O RUORWXQKVXTQJJ-UHFFFAOYSA-N 0.000 description 2
- SRLHDEROUKFEMJ-UHFFFAOYSA-N 4-methyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2C(C)CCC(=O)C2=C1 SRLHDEROUKFEMJ-UHFFFAOYSA-N 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
- C07C45/63—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 introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/571,941 US3954983A (en) | 1975-04-28 | 1975-04-28 | Triazolobenzocycloalkylthiadiazine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049011A true CA1049011A (en) | 1979-02-20 |
Family
ID=24285689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA76246112A Expired CA1049011A (en) | 1975-04-28 | 1976-02-19 | Triazolobenzocycloalkylthiadiazine derivatives |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3954983A (en, 2012) |
| JP (1) | JPS51127100A (en, 2012) |
| BE (1) | BE839035A (en, 2012) |
| CA (1) | CA1049011A (en, 2012) |
| CH (1) | CH619237A5 (en, 2012) |
| DE (1) | DE2607570A1 (en, 2012) |
| DK (1) | DK140502B (en, 2012) |
| ES (1) | ES444925A1 (en, 2012) |
| FR (1) | FR2309229A1 (en, 2012) |
| GB (1) | GB1492163A (en, 2012) |
| IE (1) | IE42419B1 (en, 2012) |
| IL (1) | IL49102A (en, 2012) |
| NL (1) | NL7601321A (en, 2012) |
| NO (1) | NO760329L (en, 2012) |
| PH (1) | PH11476A (en, 2012) |
| SE (1) | SE7601209L (en, 2012) |
| ZA (1) | ZA76621B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9908752D0 (en) * | 1999-04-16 | 1999-06-09 | Bp Oil Int | Purification process |
| DE10041478A1 (de) * | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung |
| US20030027793A1 (en) * | 2001-05-08 | 2003-02-06 | Thomas Lauterback | Transdermal treatment of parkinson's disease |
| US20030026830A1 (en) * | 2001-05-08 | 2003-02-06 | Thomas Lauterback | Transdermal therapeutic system for parkinson's disease inducing high plasma levels of rotigotine |
-
1975
- 1975-04-28 US US05/571,941 patent/US3954983A/en not_active Expired - Lifetime
-
1976
- 1976-02-02 NO NO760329*[A patent/NO760329L/no unknown
- 1976-02-03 ZA ZA621A patent/ZA76621B/xx unknown
- 1976-02-03 IE IE210/76A patent/IE42419B1/en unknown
- 1976-02-04 SE SE7601209A patent/SE7601209L/xx unknown
- 1976-02-04 DK DK45876AA patent/DK140502B/da unknown
- 1976-02-05 GB GB4487/76A patent/GB1492163A/en not_active Expired
- 1976-02-05 ES ES444925A patent/ES444925A1/es not_active Expired
- 1976-02-10 NL NL7601321A patent/NL7601321A/xx not_active Application Discontinuation
- 1976-02-13 PH PH18101A patent/PH11476A/en unknown
- 1976-02-19 CA CA76246112A patent/CA1049011A/en not_active Expired
- 1976-02-24 FR FR7605111A patent/FR2309229A1/fr active Granted
- 1976-02-25 DE DE19762607570 patent/DE2607570A1/de not_active Withdrawn
- 1976-02-25 IL IL49102A patent/IL49102A/xx unknown
- 1976-02-27 BE BE164728A patent/BE839035A/xx unknown
- 1976-02-27 CH CH245576A patent/CH619237A5/de not_active IP Right Cessation
- 1976-03-31 JP JP51034588A patent/JPS51127100A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ZA76621B (en) | 1977-01-26 |
| FR2309229B1 (en, 2012) | 1978-11-10 |
| AU1080676A (en) | 1977-08-11 |
| DE2607570A1 (de) | 1976-11-11 |
| ES444925A1 (es) | 1977-04-16 |
| NO760329L (en, 2012) | 1976-10-29 |
| FR2309229A1 (fr) | 1976-11-26 |
| US3954983A (en) | 1976-05-04 |
| GB1492163A (en) | 1977-11-16 |
| IE42419L (en) | 1976-10-28 |
| DK140502B (da) | 1979-09-17 |
| IL49102A0 (en) | 1976-04-30 |
| CH619237A5 (en, 2012) | 1980-09-15 |
| BE839035A (fr) | 1976-06-16 |
| IE42419B1 (en) | 1980-07-30 |
| DK45876A (en, 2012) | 1976-10-29 |
| PH11476A (en) | 1978-02-01 |
| JPS51127100A (en) | 1976-11-05 |
| DK140502C (en, 2012) | 1980-02-11 |
| NL7601321A (nl) | 1976-11-01 |
| IL49102A (en) | 1978-07-31 |
| SE7601209L (sv) | 1976-10-29 |
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