SU526289A3 - Способ получени производных тиендиазепина - Google Patents
Способ получени производных тиендиазепинаInfo
- Publication number
- SU526289A3 SU526289A3 SU1809322A SU1809322A SU526289A3 SU 526289 A3 SU526289 A3 SU 526289A3 SU 1809322 A SU1809322 A SU 1809322A SU 1809322 A SU1809322 A SU 1809322A SU 526289 A3 SU526289 A3 SU 526289A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- chloroform
- thiophene
- amino
- recrystallized
- tetramethylene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 27
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 16
- 229930192474 thiophene Natural products 0.000 claims 14
- 239000000047 product Substances 0.000 claims 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- -1 m-nitrobenzoyl Chemical group 0.000 claims 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 239000007787 solid Substances 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- WQINSVOOIJDOLJ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetic acid Chemical compound C1=CC=C2C(=O)N(CC(=O)O)C(=O)C2=C1 WQINSVOOIJDOLJ-UHFFFAOYSA-N 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 4
- OGDWOTGXUXNSQA-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetamide Chemical compound C1=CC=C2C(=O)N(CC(=O)N)C(=O)C2=C1 OGDWOTGXUXNSQA-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 238000007363 ring formation reaction Methods 0.000 claims 3
- 238000003756 stirring Methods 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- 230000010933 acylation Effects 0.000 claims 2
- 238000005917 acylation reaction Methods 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 239000008096 xylene Substances 0.000 claims 2
- PEBGIHXZACIBNZ-UHFFFAOYSA-N (2-amino-4-methylthiophen-3-yl)-phenylmethanone Chemical compound CC1=CSC(N)=C1C(=O)C1=CC=CC=C1 PEBGIHXZACIBNZ-UHFFFAOYSA-N 0.000 claims 1
- VXIMIQNIBMDZCM-UHFFFAOYSA-N (2-aminothiophen-3-yl)-phenylmethanone Chemical compound S1C=CC(C(=O)C=2C=CC=CC=2)=C1N VXIMIQNIBMDZCM-UHFFFAOYSA-N 0.000 claims 1
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- JYOUFPNYTOFCSJ-UHFFFAOYSA-N 3-(4-chlorophenyl)-3-oxopropanenitrile Chemical compound ClC1=CC=C(C(=O)CC#N)C=C1 JYOUFPNYTOFCSJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- VGHOWOWLIXPTOA-UHFFFAOYSA-N cyclohexane;toluene Chemical compound C1CCCCC1.CC1=CC=CC=C1 VGHOWOWLIXPTOA-UHFFFAOYSA-N 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical class NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 claims 1
- 150000003577 thiophenes Chemical class 0.000 claims 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 claims 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
-
- 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
- C07D333/26—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 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (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 |
|---|---|---|---|
| ES393101A ES393101A1 (es) | 1971-07-09 | 1971-07-09 | Procedimiento para la preparacion de derivados de tieno- diazepina. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU526289A3 true SU526289A3 (ru) | 1976-08-25 |
Family
ID=8458749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1809322A SU526289A3 (ru) | 1971-07-09 | 1972-07-08 | Способ получени производных тиендиазепина |
Country Status (14)
| Country | Link |
|---|---|
| AR (1) | AR196408A1 (https=) |
| AT (1) | AT331799B (https=) |
| BE (1) | BE785998A (https=) |
| CH (1) | CH566338A5 (https=) |
| DE (1) | DE2233457A1 (https=) |
| ES (1) | ES393101A1 (https=) |
| FR (1) | FR2145503B1 (https=) |
| GB (1) | GB1409554A (https=) |
| HU (1) | HU167935B (https=) |
| NL (1) | NL7209461A (https=) |
| RO (1) | RO61516A (https=) |
| SE (1) | SE397350B (https=) |
| SU (1) | SU526289A3 (https=) |
| ZA (1) | ZA724697B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2158739C2 (ru) * | 1995-02-08 | 2000-11-10 | Такеда Кемикал Индастриз, Лтд. | Соединения тиенопиримидина, способ их получения, фармацевтическая композиция |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH30676A (en) * | 1986-07-22 | 1997-09-16 | Boehringer Ingelhein Kg | Hetrazepine compounds which have useful pharmaceutical utility |
| US6727258B2 (en) | 1997-10-29 | 2004-04-27 | King Pharmaceutical Research & Development, Inc. | Allosteric adenosine receptor modulators |
| US6323214B1 (en) | 1997-10-29 | 2001-11-27 | Medco Research, Inc | Allosteric adenosine receptor modulators |
| US5939432A (en) * | 1997-10-29 | 1999-08-17 | Medco Research, Inc. | Thiophenes useful for modulating the adenosine receptor |
-
1971
- 1971-07-09 ES ES393101A patent/ES393101A1/es not_active Expired
-
1972
- 1972-07-05 HU HUMA2378A patent/HU167935B/hu unknown
- 1972-07-06 SE SE7208936A patent/SE397350B/xx unknown
- 1972-07-06 GB GB3175272A patent/GB1409554A/en not_active Expired
- 1972-07-06 FR FR7224523A patent/FR2145503B1/fr not_active Expired
- 1972-07-07 DE DE2233457A patent/DE2233457A1/de active Pending
- 1972-07-07 AR AR242961A patent/AR196408A1/es active
- 1972-07-07 NL NL7209461A patent/NL7209461A/xx not_active Application Discontinuation
- 1972-07-07 BE BE785998A patent/BE785998A/xx unknown
- 1972-07-07 ZA ZA724697A patent/ZA724697B/xx unknown
- 1972-07-07 CH CH1017872A patent/CH566338A5/xx not_active IP Right Cessation
- 1972-07-08 SU SU1809322A patent/SU526289A3/ru active
- 1972-07-10 AT AT591572A patent/AT331799B/de not_active IP Right Cessation
- 1972-07-10 RO RO71562A patent/RO61516A/ro unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2158739C2 (ru) * | 1995-02-08 | 2000-11-10 | Такеда Кемикал Индастриз, Лтд. | Соединения тиенопиримидина, способ их получения, фармацевтическая композиция |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2233457A1 (de) | 1973-02-22 |
| ES393101A1 (es) | 1974-05-16 |
| AU4432972A (en) | 1974-01-10 |
| BE785998A (fr) | 1972-11-03 |
| FR2145503A1 (https=) | 1973-02-23 |
| SE397350B (sv) | 1977-10-31 |
| NL7209461A (https=) | 1973-01-11 |
| AR196408A1 (es) | 1973-12-27 |
| ATA591572A (de) | 1975-12-15 |
| CH566338A5 (https=) | 1975-09-15 |
| AT331799B (de) | 1976-08-25 |
| FR2145503B1 (https=) | 1975-10-17 |
| RO61516A (https=) | 1977-04-15 |
| ZA724697B (en) | 1973-04-25 |
| HU167935B (https=) | 1976-01-28 |
| GB1409554A (en) | 1975-10-08 |
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