JPS627197B2 - - Google Patents
Info
- Publication number
- JPS627197B2 JPS627197B2 JP8671077A JP8671077A JPS627197B2 JP S627197 B2 JPS627197 B2 JP S627197B2 JP 8671077 A JP8671077 A JP 8671077A JP 8671077 A JP8671077 A JP 8671077A JP S627197 B2 JPS627197 B2 JP S627197B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrobromide
- formula
- mmol
- thienomorphan
- methyl
- 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
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 5
- -1 tetrahydrofurfuryl Chemical group 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- ZPAPCUKKKOSLPZ-UHFFFAOYSA-N morphan Chemical compound C1CNC2CCCC1C2 ZPAPCUKKKOSLPZ-UHFFFAOYSA-N 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 238000004364 calculation method Methods 0.000 description 5
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 1
- VOHILFSOWRNVJJ-UHFFFAOYSA-N 2-(bromomethyl)oxolane Chemical compound BrCC1CCCO1 VOHILFSOWRNVJJ-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8671077A JPS5422396A (en) | 1977-07-21 | 1977-07-21 | Preparation of thienomorphan derivative and its salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8671077A JPS5422396A (en) | 1977-07-21 | 1977-07-21 | Preparation of thienomorphan derivative and its salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5422396A JPS5422396A (en) | 1979-02-20 |
| JPS627197B2 true JPS627197B2 (enrdf_load_stackoverflow) | 1987-02-16 |
Family
ID=13894461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8671077A Granted JPS5422396A (en) | 1977-07-21 | 1977-07-21 | Preparation of thienomorphan derivative and its salt |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5422396A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5175284A (en) * | 1991-10-15 | 1992-12-29 | Merck & Co., Inc. | Tricyclic thienothiopyrans as pharmaceutical intermediates |
-
1977
- 1977-07-21 JP JP8671077A patent/JPS5422396A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5422396A (en) | 1979-02-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CZ200062A3 (cs) | Způsob výroby citalopramu | |
| CN113365992B (zh) | 用于沃塞洛托的制备的方法和中间体 | |
| US4001223A (en) | Adamantane-piperazine derivatives | |
| KR920002295B1 (ko) | 프롤리디논 유도체의 제조방법 | |
| KR900005956B1 (ko) | 1,4-디하이드로피리딘-3,5-디카르복실산의 비대칭 에스테르 유도체의 제조방법 | |
| JPS627197B2 (enrdf_load_stackoverflow) | ||
| JPH0352465B2 (enrdf_load_stackoverflow) | ||
| JPS6317077B2 (enrdf_load_stackoverflow) | ||
| JPS6135194B2 (enrdf_load_stackoverflow) | ||
| Demopoulos et al. | Synthesis of 6, 7, 8, 9‐tetrahydro‐N, N‐di‐n‐propyl‐1H‐benz [g] indol‐7‐amine, a potential dopamine receptor agonist | |
| US4009172A (en) | 2,3,3A,6,7,7A-Hexahydro-thieno[3,2-b]pyridin-(4H)5-ones | |
| Murai et al. | Aldol-type condensation reactions of lithium eneselenolates generated from selenoamides with aldehydes | |
| JPS6115076B2 (enrdf_load_stackoverflow) | ||
| JP2004500413A (ja) | Ｎ−ヒドロキシルアミンの選択的ｎ−ホルミル化の方法 | |
| SU1038341A1 (ru) | Способ получени @ -арилиндолотриметинцианинов | |
| SU1532556A1 (ru) | Способ получени Е-1-метил-1-метоксикарбонил-2-этоксикарбонилциклопропана | |
| JPS63211264A (ja) | インドリン類の製造法 | |
| US3949091A (en) | 8-Substituted dibenzobicyclo[3.2.1]octadienes for treating depression | |
| US3960944A (en) | 8-Carboxamide dibenzobicyclo(3.2.1)octadienes | |
| JPS6115077B2 (enrdf_load_stackoverflow) | ||
| JPH0699402B2 (ja) | ４，４‐ジブロモ‐１，３‐ジメチル‐２‐ピラゾリン‐５‐オン及びその製造方法 | |
| JPH03258768A (ja) | １，３，５―パーヒドロトリアジン―２，４，６―トリチオン誘導体の製造方法 | |
| JPS5852995B2 (ja) | フルフラ−ル誘導体の製造法 | |
| KR20050062944A (ko) | 디이소프로필((1-((2-아미노-6-클로로-9ｈ-퓨린-9-일)메틸)사이클로프로필)옥시)-메틸포스포네이트의 새로운 제조방법 | |
| JPS5910358B2 (ja) | 新規エルゴリン誘導体 |