CS244907B2 - Preparation method of 2,4-diamino-5-/3,4,5-trimethoxybenzyl/-pyriminine - Google Patents
Preparation method of 2,4-diamino-5-/3,4,5-trimethoxybenzyl/-pyriminine Download PDFInfo
- Publication number
- CS244907B2 CS244907B2 CS824716A CS471682A CS244907B2 CS 244907 B2 CS244907 B2 CS 244907B2 CS 824716 A CS824716 A CS 824716A CS 471682 A CS471682 A CS 471682A CS 244907 B2 CS244907 B2 CS 244907B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- guanidine
- benzylisomer
- reacted
- compound
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 title description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 26
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 13
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims abstract description 13
- -1 alkali metal alkoxide Chemical class 0.000 claims abstract description 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 238000000926 separation method Methods 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract 2
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims description 8
- 229960001082 trimethoprim Drugs 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OOWFYDWAMOKVSF-UHFFFAOYSA-N 3-methoxypropanenitrile Chemical compound COCCC#N OOWFYDWAMOKVSF-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Liquid Crystal Substances (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU811868A HU186413B (en) | 1981-06-26 | 1981-06-26 | Process for producing 2,4-diamino-5-bracket-3-comma above,4-comma above,5-comma above-trimethoxy-benzyl-bracket closed-pyrimidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS471682A2 CS471682A2 (en) | 1985-09-17 |
| CS244907B2 true CS244907B2 (en) | 1986-08-14 |
Family
ID=10956590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS824716A CS244907B2 (en) | 1981-06-26 | 1982-06-24 | Preparation method of 2,4-diamino-5-/3,4,5-trimethoxybenzyl/-pyriminine |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5838265A (ro) |
| AT (1) | AT385033B (ro) |
| AU (1) | AU547822B2 (ro) |
| BE (1) | BE893609A (ro) |
| CA (1) | CA1164458A (ro) |
| CH (1) | CH651828A5 (ro) |
| CS (1) | CS244907B2 (ro) |
| DD (1) | DD202702A5 (ro) |
| DK (1) | DK155668C (ro) |
| ES (1) | ES8304948A1 (ro) |
| FI (1) | FI76789C (ro) |
| FR (1) | FR2508449B1 (ro) |
| GB (1) | GB2106098B (ro) |
| GR (1) | GR76158B (ro) |
| HU (1) | HU186413B (ro) |
| IE (1) | IE53347B1 (ro) |
| IL (1) | IL66131A (ro) |
| IT (1) | IT1190888B (ro) |
| RO (1) | RO85316B (ro) |
| SE (1) | SE451134B (ro) |
| SU (1) | SU1147252A3 (ro) |
| YU (1) | YU42264B (ro) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1303727B (de) * | 1959-09-03 | 1976-02-05 | Ausscheidung aus: 14 45 176 The Wellcome Foundation Ltd., London | Alpha-Arylidensubstituierte Propioni-Irile |
| NL122146C (ro) * | 1960-09-02 | |||
| DE2635765C3 (de) * | 1976-08-09 | 1979-02-08 | Ludwig Heumann & Co Gmbh, 8500 Nuernberg | Verfahren zur Herstellung von 2,4-EMamino-5-(3',4'r5'-trimethoxybenzyl)-pyrimidin |
| US4115650A (en) * | 1976-11-17 | 1978-09-19 | Hoffmann-La Roche Inc. | Process for preparing 2,4-diamino-5-(substituted benzyl)-pyrimidines |
| DE2730467A1 (de) * | 1977-07-06 | 1979-01-18 | Basf Ag | Benzylpyrimidine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
-
1981
- 1981-06-26 HU HU811868A patent/HU186413B/hu not_active IP Right Cessation
-
1982
- 1982-06-18 DK DK275682A patent/DK155668C/da not_active IP Right Cessation
- 1982-06-23 BE BE1/10542A patent/BE893609A/fr not_active IP Right Cessation
- 1982-06-23 SE SE8203913A patent/SE451134B/sv not_active IP Right Cessation
- 1982-06-24 AT AT0244882A patent/AT385033B/de not_active IP Right Cessation
- 1982-06-24 FI FI822267A patent/FI76789C/fi not_active IP Right Cessation
- 1982-06-24 RO RO107980A patent/RO85316B/ro unknown
- 1982-06-24 IT IT22034/82A patent/IT1190888B/it active
- 1982-06-24 SU SU823456105A patent/SU1147252A3/ru active
- 1982-06-24 GR GR68559A patent/GR76158B/el unknown
- 1982-06-24 CS CS824716A patent/CS244907B2/cs unknown
- 1982-06-24 IL IL66131A patent/IL66131A/xx unknown
- 1982-06-24 DD DD82241053A patent/DD202702A5/de not_active IP Right Cessation
- 1982-06-24 GB GB08218309A patent/GB2106098B/en not_active Expired
- 1982-06-25 IE IE1521/82A patent/IE53347B1/en not_active IP Right Cessation
- 1982-06-25 YU YU1384/82A patent/YU42264B/xx unknown
- 1982-06-25 CH CH3907/82A patent/CH651828A5/de not_active IP Right Cessation
- 1982-06-25 AU AU85345/82A patent/AU547822B2/en not_active Ceased
- 1982-06-25 FR FR8211150A patent/FR2508449B1/fr not_active Expired
- 1982-06-25 CA CA000405973A patent/CA1164458A/en not_active Expired
- 1982-06-25 ES ES513481A patent/ES8304948A1/es not_active Expired
- 1982-06-25 JP JP57109646A patent/JPS5838265A/ja active Pending
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