NO753480L - - Google Patents
Info
- Publication number
- NO753480L NO753480L NO753480A NO753480A NO753480L NO 753480 L NO753480 L NO 753480L NO 753480 A NO753480 A NO 753480A NO 753480 A NO753480 A NO 753480A NO 753480 L NO753480 L NO 753480L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- pyrimidine
- diamino
- water
- hydroxy
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- SWELIMKTDYHAOY-UHFFFAOYSA-N 2,4-diamino-6-hydroxypyrimidine Chemical compound NC1=CC(=O)N=C(N)N1 SWELIMKTDYHAOY-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 10
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- -1 amino-substituted pyrimidines Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 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 description 4
- FYJKTYLNKCUCLP-UHFFFAOYSA-N 6-hydroxytrimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2N)O)=C1 FYJKTYLNKCUCLP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229960001082 trimethoprim Drugs 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- XXRUQNNAKXZSOS-UHFFFAOYSA-N 5-(chloromethyl)-1,2,3-trimethoxybenzene Chemical compound COC1=CC(CCl)=CC(OC)=C1OC XXRUQNNAKXZSOS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XQCZBXHVTFVIFE-UHFFFAOYSA-N 2-amino-4-hydroxypyrimidine Chemical compound NC1=NC=CC(O)=N1 XQCZBXHVTFVIFE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7413202A SE400077B (sv) | 1974-10-21 | 1974-10-21 | Ett forfarande for framstellning av 2,4-diamino-5(3',4',5',-trimetoxibensyl)-pyrimidin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO753480L true NO753480L (enrdf_load_html_response) | 1976-04-22 |
Family
ID=20322479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO753480A NO753480L (enrdf_load_html_response) | 1974-10-21 | 1975-10-15 |
Country Status (13)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE21901T1 (de) * | 1982-07-30 | 1986-09-15 | Smith Kline French Lab | Aminopyrimidinone und ihre herstellung. |
| CN118560124B (zh) * | 2024-07-30 | 2024-11-19 | 如东鑫利纺织有限公司 | 一种抗菌透气的针织面料及其制备方法 |
-
1974
- 1974-10-21 SE SE7413202A patent/SE400077B/xx unknown
-
1975
- 1975-10-13 CH CH1326475A patent/CH599168A5/xx not_active IP Right Cessation
- 1975-10-15 NO NO753480A patent/NO753480L/no unknown
- 1975-10-16 DK DK465375AA patent/DK135375B/da unknown
- 1975-10-16 AT AT788475A patent/AT343122B/de not_active IP Right Cessation
- 1975-10-17 DE DE19752546510 patent/DE2546510A1/de active Pending
- 1975-10-17 FI FI752900A patent/FI752900A7/fi not_active Application Discontinuation
- 1975-10-20 GB GB42995/75A patent/GB1526235A/en not_active Expired
- 1975-10-20 FR FR7532021A patent/FR2299326A1/fr active Granted
- 1975-10-21 JP JP50126016A patent/JPS5165776A/ja active Pending
- 1975-10-21 NL NL7512341A patent/NL7512341A/xx not_active Application Discontinuation
- 1975-10-21 BE BE161097A patent/BE834694A/xx unknown
- 1975-10-21 LU LU73620A patent/LU73620A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU73620A1 (enrdf_load_html_response) | 1976-08-19 |
| SE400077B (sv) | 1978-03-13 |
| BE834694A (fr) | 1976-04-21 |
| DK465375A (enrdf_load_html_response) | 1976-04-22 |
| DK135375B (da) | 1977-04-18 |
| JPS5165776A (en) | 1976-06-07 |
| FR2299326A1 (fr) | 1976-08-27 |
| ATA788475A (de) | 1977-09-15 |
| GB1526235A (en) | 1978-09-27 |
| NL7512341A (nl) | 1976-04-23 |
| FR2299326B1 (enrdf_load_html_response) | 1978-10-13 |
| DE2546510A1 (de) | 1976-04-29 |
| CH599168A5 (enrdf_load_html_response) | 1978-05-12 |
| AT343122B (de) | 1978-05-10 |
| FI752900A7 (enrdf_load_html_response) | 1976-04-22 |
| SE7413202L (sv) | 1976-04-22 |
| DK135375C (enrdf_load_html_response) | 1977-10-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU1021342A3 (ru) | Способ получени производных пиперидинопропила или их фармацевтически приемлемых солей | |
| SK283652B6 (sk) | Spôsob prípravy N,N,6-trimetyl-2-(4-metylfenyl)imidazo-[1,2- a]pyridín-3-acetamidu a jeho solí | |
| NO753480L (enrdf_load_html_response) | ||
| US4963678A (en) | Process for large-scale production of BMY 21502 | |
| US5734055A (en) | Process for preparing N-tert-butyl-2-pyrazinecarboxamide and N-tert-butyl-2-piperazinecarboxamide | |
| DK170331B1 (da) | Fremgangsmåde til fremstilling af rimantadin | |
| US7642279B2 (en) | Atipamezole hydrochloride crystallization method | |
| EP0252353A1 (de) | 4-Benzyloxy-3-pyrrolin-2-on-1-yl-acetamid, dessen Herstellung und Verwendung | |
| JP3088561B2 (ja) | ２，３−ジアミノピリジン類の製造方法 | |
| US7728147B2 (en) | Detomidine hydrochloride crystallization method | |
| US4777255A (en) | Process for preparing a purine derivative | |
| CN115215835B (zh) | 一种2-(2-(2,6-二氧哌啶-3-基)-1-氧异吲哚啉-4-基)乙酸的制备方法 | |
| HU186528B (en) | Process for producing tetronnoic acid | |
| JP2682713B2 (ja) | 光学活性テトラヒドロフランの製法 | |
| CN108623608B (zh) | 扎布沙星中间体的制备方法 | |
| EP0071741A1 (en) | Process for producing 2,4-diamino-(3,5-dimethoxy-4-methoxy-ethoxy-benzyl)-pyrimidine | |
| US2785162A (en) | Process for the formylation of a 5 nitrosouracil | |
| US4552967A (en) | Process for the synthesis of intermediates in the preparation of diaminopyridines | |
| US6066744A (en) | Process for producing 5-methylindolines | |
| JP3544694B2 (ja) | Ｎ−ｔｅｒｔ−ブチル−２−ピペラジンカルボキサミド類の製造法 | |
| US2496326A (en) | Production of a 3-(lower acyl) amino-3-carbalkoxy-2-piperidones | |
| JP4099630B2 (ja) | パーフルオロアルキル化合物の製造方法 | |
| AU764168B2 (en) | Method for preparing 5-(1-methylethyl)-6-(phenylmethyl) pyrimidine-2,4(1H,3H)-dione | |
| JP2762106B2 (ja) | ３―ヒドロキシピロリジンの製造方法 | |
| JP4263427B2 (ja) | ハロゲノ−４−ジヒドロキシメチルピリジン、その製造法及びそれを用いたハロゲノ−４−ピリジンカルバルデヒドの製造法 |