SU474990A3 - Способ получени производных оксазоло(4,5- ) азепина - Google Patents
Способ получени производных оксазоло(4,5- ) азепинаInfo
- Publication number
- SU474990A3 SU474990A3 SU1878315A SU1878315A SU474990A3 SU 474990 A3 SU474990 A3 SU 474990A3 SU 1878315 A SU1878315 A SU 1878315A SU 1878315 A SU1878315 A SU 1878315A SU 474990 A3 SU474990 A3 SU 474990A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carried out
- oxazolo
- azepine
- reaction
- mol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 title description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 18
- 239000004202 carbamide Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- -1 hydroxy, carboxy Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 229920006395 saturated elastomer Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PJHKXESPJOFGOA-UHFFFAOYSA-N 1h-azepine;dihydrochloride Chemical compound Cl.Cl.N1C=CC=CC=C1 PJHKXESPJOFGOA-UHFFFAOYSA-N 0.000 description 4
- AJUMGSLQADLWKL-UHFFFAOYSA-N 1h-azepine;hydrochloride Chemical compound Cl.N1C=CC=CC=C1 AJUMGSLQADLWKL-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Pulmonology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Measurement Of Radiation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2206385A DE2206385C2 (de) | 1972-02-10 | 1972-02-10 | 2-Amino-4,5,7,8-tetrahydro-6H-oxazolo-[4,5-d]azepinderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU474990A3 true SU474990A3 (ru) | 1975-06-25 |
Family
ID=5835665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1878315A SU474990A3 (ru) | 1972-02-10 | 1973-01-31 | Способ получени производных оксазоло(4,5- ) азепина |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5825678B2 (enExample) |
| KR (1) | KR780000196B1 (enExample) |
| AT (1) | AT321296B (enExample) |
| BE (1) | BE795257A (enExample) |
| BG (1) | BG22826A3 (enExample) |
| CA (1) | CA997342A (enExample) |
| CH (1) | CH576476A5 (enExample) |
| CS (1) | CS181231B2 (enExample) |
| DD (1) | DD104083A5 (enExample) |
| DE (1) | DE2206385C2 (enExample) |
| DK (1) | DK137011C (enExample) |
| FI (1) | FI54126C (enExample) |
| FR (1) | FR2181718B1 (enExample) |
| GB (1) | GB1412377A (enExample) |
| HU (1) | HU165459B (enExample) |
| IE (1) | IE37347B1 (enExample) |
| IL (1) | IL41512A (enExample) |
| NL (1) | NL173525C (enExample) |
| NO (1) | NO131599C (enExample) |
| PL (1) | PL84740B1 (enExample) |
| RO (1) | RO61191A (enExample) |
| SE (1) | SE380805B (enExample) |
| SU (1) | SU474990A3 (enExample) |
| ZA (1) | ZA73924B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2776106C2 (ru) * | 2018-01-26 | 2022-07-13 | Сионоги Энд Ко., Лтд. | Конденсированные кольцевые соединения, обладающие антагонистическим действием в отношении d3-рецептора дофамина |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3820775A1 (de) * | 1988-06-20 | 1989-12-21 | Thomae Gmbh Dr K | Neue 4,5,7,8-tetrahydro-6h-thiazolo(5,4,-d)azepine, ihre herstellung und ihre verwendung als arzneimittel |
| DE4345224C2 (de) * | 1993-12-18 | 1999-07-01 | Asta Medica Ag | Verfahren zur Herstellung von Säureadditionssalzen des Azelastins und Flezelastins |
| CL2004000553A1 (es) | 2003-03-20 | 2005-02-04 | Actelion Pharmaceuticals Ltd | Uso de compuestos derivados de guanidina como antagonistas del receptor de neuropeptido ff; compuestos derivados de guanidina; procedimientos de preparacion; y composicion farmaceutica que los comprende. |
| AU2004270304A1 (en) | 2003-09-05 | 2005-03-17 | Actelion Pharmaceuticals Ltd. | Guanidine derivatives |
| JPWO2010024258A1 (ja) * | 2008-08-29 | 2012-01-26 | 塩野義製薬株式会社 | Ｐｉ３ｋ阻害活性を有する縮環アゾール誘導体 |
| CN105706280A (zh) | 2013-11-11 | 2016-06-22 | 株式会社神户制钢所 | 钛制燃料电池隔板材及钛制燃料电池隔板材的制造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2040510C3 (de) * | 1970-08-14 | 1980-03-06 | Dr. Karl Thomae Gmbh, 7950 Biberach | Oxazole- und Thiazole eckige Klammer auf 5,4-d] azepin- Derivate |
| BG17968A3 (bg) * | 1970-08-14 | 1974-03-05 | Dr. Karl Thomae Gmbh | Метод за получаване на производни на азепина |
| ZA756062B (en) * | 1975-09-23 | 1977-04-27 | M Schoeman | Supplying fuel to internal combustion engines |
-
0
- BE BE795257D patent/BE795257A/xx not_active IP Right Cessation
-
1972
- 1972-02-10 DE DE2206385A patent/DE2206385C2/de not_active Expired
-
1973
- 1973-01-18 NL NLAANVRAGE7300744,A patent/NL173525C/xx not_active IP Right Cessation
- 1973-01-29 AT AT73473A patent/AT321296B/de not_active IP Right Cessation
- 1973-01-29 DD DD168504A patent/DD104083A5/xx unknown
- 1973-01-31 SU SU1878315A patent/SU474990A3/ru active
- 1973-02-07 KR KR7300224A patent/KR780000196B1/ko not_active Expired
- 1973-02-08 BG BG022667A patent/BG22826A3/xx unknown
- 1973-02-08 CH CH187273A patent/CH576476A5/xx not_active IP Right Cessation
- 1973-02-08 HU HUTO898A patent/HU165459B/hu unknown
- 1973-02-08 SE SE7301773A patent/SE380805B/xx unknown
- 1973-02-09 IE IE211/73A patent/IE37347B1/xx unknown
- 1973-02-09 NO NO533/73A patent/NO131599C/no unknown
- 1973-02-09 IL IL41512A patent/IL41512A/xx unknown
- 1973-02-09 FR FR7304643A patent/FR2181718B1/fr not_active Expired
- 1973-02-09 ZA ZA730924A patent/ZA73924B/xx unknown
- 1973-02-09 FI FI394/73A patent/FI54126C/fi active
- 1973-02-09 GB GB647673A patent/GB1412377A/en not_active Expired
- 1973-02-09 CS CS7300000974A patent/CS181231B2/cs unknown
- 1973-02-09 DK DK74573A patent/DK137011C/da not_active IP Right Cessation
- 1973-02-09 PL PL1973160658A patent/PL84740B1/pl unknown
- 1973-02-09 JP JP48016407A patent/JPS5825678B2/ja not_active Expired
- 1973-02-09 CA CA163,409A patent/CA997342A/en not_active Expired
- 1973-02-10 RO RO73806A patent/RO61191A/ro unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2776106C2 (ru) * | 2018-01-26 | 2022-07-13 | Сионоги Энд Ко., Лтд. | Конденсированные кольцевые соединения, обладающие антагонистическим действием в отношении d3-рецептора дофамина |
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