DE2204201A1 - Verfahren zur Herstellung von neuen 3,4-Dihydro-thieno eckige Klammer auf 2,3d eckige Klammer zu eckige Klammer auf 1,2,3 eckige Klammer zu triazin-4-on-Derivaten und ihren Salzen - Google Patents
Verfahren zur Herstellung von neuen 3,4-Dihydro-thieno eckige Klammer auf 2,3d eckige Klammer zu eckige Klammer auf 1,2,3 eckige Klammer zu triazin-4-on-Derivaten und ihren SalzenInfo
- Publication number
- DE2204201A1 DE2204201A1 DE19722204201 DE2204201A DE2204201A1 DE 2204201 A1 DE2204201 A1 DE 2204201A1 DE 19722204201 DE19722204201 DE 19722204201 DE 2204201 A DE2204201 A DE 2204201A DE 2204201 A1 DE2204201 A1 DE 2204201A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- methyl
- square brackets
- compounds
- ethyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 16
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical class O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000003839 salts Chemical class 0.000 title description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 235000010288 sodium nitrite Nutrition 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 150000001447 alkali salts Chemical class 0.000 claims description 5
- 238000006193 diazotization reaction Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- WHZIZZOTISTHCT-UHFFFAOYSA-N 2-aminothiophene-3-carboxamide Chemical class NC(=O)C=1C=CSC=1N WHZIZZOTISTHCT-UHFFFAOYSA-N 0.000 claims description 3
- 239000012435 aralkylating agent Substances 0.000 claims description 3
- 239000012954 diazonium Substances 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 claims description 2
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- 150000003459 sulfonic acid esters Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000012043 crude product Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001677 (2R,5R)-1,4-dithiane-2,5-diol Substances 0.000 description 1
- -1 -CH2CQ-C5H5) Chemical class 0.000 description 1
- YUIOPHXTILULQC-UHFFFAOYSA-N 1,4-Dithiane-2,5-diol Chemical compound OC1CSC(O)CS1 YUIOPHXTILULQC-UHFFFAOYSA-N 0.000 description 1
- FFAKFORHXDNYEN-UHFFFAOYSA-N 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide Chemical compound C1CCCC2=C1SC(N)=C2C(=O)N FFAKFORHXDNYEN-UHFFFAOYSA-N 0.000 description 1
- ZKXSEMXZKAQARN-UHFFFAOYSA-N 2-amino-4,5-dimethylthiophene-3-carboxamide Chemical compound CC=1SC(N)=C(C(N)=O)C=1C ZKXSEMXZKAQARN-UHFFFAOYSA-N 0.000 description 1
- DVGHAYAFIHAXOR-UHFFFAOYSA-N 2-amino-5-methylthiophene-3-carboxamide Chemical compound CC1=CC(C(N)=O)=C(N)S1 DVGHAYAFIHAXOR-UHFFFAOYSA-N 0.000 description 1
- GZPPSXCHBNAOKH-UHFFFAOYSA-N 2-amino-n-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide Chemical compound C1CCCC2=C1SC(N)=C2C(=O)NC GZPPSXCHBNAOKH-UHFFFAOYSA-N 0.000 description 1
- LIHUTSFYFGCWQP-UHFFFAOYSA-N 2-cyano-n-methylacetamide Chemical compound CNC(=O)CC#N LIHUTSFYFGCWQP-UHFFFAOYSA-N 0.000 description 1
- JRNMITOICVFZHK-UHFFFAOYSA-N 3-methyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]triazin-4-one Chemical compound C1CCCC2=C1SC1=C2C(=O)N(C)N=N1 JRNMITOICVFZHK-UHFFFAOYSA-N 0.000 description 1
- AUMYBOLSUBPAEF-UHFFFAOYSA-N 3h-thieno[2,3-d]triazin-4-one Chemical compound O=C1NN=NC2=C1C=CS2 AUMYBOLSUBPAEF-UHFFFAOYSA-N 0.000 description 1
- LBNCCMAHONWTQC-UHFFFAOYSA-N 5,6-dimethyl-3h-thieno[2,3-d]triazin-4-one Chemical compound N1=NNC(=O)C2=C1SC(C)=C2C LBNCCMAHONWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000010792 warming 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
-
- 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
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT90271A AT303049B (de) | 1971-02-03 | 1971-02-03 | Verfahren zur Herstellung von neuen 3,4-Dihydro-thieno-[2,3-d][1,2,3]triazin-4-on-Derivaten und ihren Salzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2204201A1 true DE2204201A1 (de) | 1972-08-31 |
Family
ID=3502471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722204201 Pending DE2204201A1 (de) | 1971-02-03 | 1972-01-29 | Verfahren zur Herstellung von neuen 3,4-Dihydro-thieno eckige Klammer auf 2,3d eckige Klammer zu eckige Klammer auf 1,2,3 eckige Klammer zu triazin-4-on-Derivaten und ihren Salzen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3772276A (enExample) |
| AT (1) | AT303049B (enExample) |
| BE (1) | BE778617A (enExample) |
| CH (1) | CH528530A (enExample) |
| DE (1) | DE2204201A1 (enExample) |
| FR (1) | FR2124203B1 (enExample) |
| GB (1) | GB1374320A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3963713A (en) * | 1975-01-17 | 1976-06-15 | Sandoz, Inc. | Furo(3,4-e)-as-triazines and corresponding 4-oxides |
| US3962240A (en) * | 1975-05-08 | 1976-06-08 | Sandoz, Inc. | Process for the preparation of furo(3,4-e)-as-triazines |
| US4055643A (en) * | 1975-06-12 | 1977-10-25 | Sandoz, Inc. | Furo(3,4-E)-as-triazines and corresponding 4-oxides as sleep inducers and minor tranquilizers |
| US4013767A (en) * | 1975-08-15 | 1977-03-22 | Sandoz, Inc. | 3-Pyridyl and pyridyl-N-oxide-furo[3,4-e]-as-triazines |
| US4018768A (en) * | 1975-12-02 | 1977-04-19 | Eli Lilly And Company | [1]Benzothieno [3,2-d]-v-triazines and synthesis thereof |
| BE1008374A3 (nl) * | 1994-04-22 | 1996-04-02 | Philips Electronics Nv | Werkwijze voor het verbinden van twee van sporenpatronen voorziene strippen, alsmede magneetkop voorzien van twee volgens de werkwijze met elkaar verbonden strippen. |
-
1971
- 1971-02-03 AT AT90271A patent/AT303049B/de not_active IP Right Cessation
- 1971-03-12 FR FR7108795A patent/FR2124203B1/fr not_active Expired
-
1972
- 1972-01-24 CH CH97972A patent/CH528530A/fr not_active IP Right Cessation
- 1972-01-28 BE BE778617A patent/BE778617A/xx unknown
- 1972-01-28 US US00221805A patent/US3772276A/en not_active Expired - Lifetime
- 1972-01-29 DE DE19722204201 patent/DE2204201A1/de active Pending
- 1972-01-31 GB GB444172A patent/GB1374320A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3772276A (en) | 1973-11-13 |
| BE778617A (fr) | 1972-05-16 |
| CH528530A (fr) | 1972-09-30 |
| FR2124203A1 (enExample) | 1972-09-22 |
| AT303049B (de) | 1972-11-10 |
| FR2124203B1 (enExample) | 1975-06-06 |
| GB1374320A (en) | 1974-11-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |