CA1050538A - Pyrimidine derivatives - Google Patents
Pyrimidine derivativesInfo
- Publication number
- CA1050538A CA1050538A CA222,322A CA222322A CA1050538A CA 1050538 A CA1050538 A CA 1050538A CA 222322 A CA222322 A CA 222322A CA 1050538 A CA1050538 A CA 1050538A
- Authority
- CA
- Canada
- Prior art keywords
- base
- neutral
- salt
- ethyl
- oxo
- 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.)
- Expired
Links
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 19
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 230000007935 neutral effect Effects 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 5
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229960005141 piperazine Drugs 0.000 claims description 8
- 150000004885 piperazines Chemical class 0.000 claims description 7
- -1 halogeno compound Chemical class 0.000 claims description 6
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 2
- 244000052616 bacterial pathogen Species 0.000 abstract description 2
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- CVVIJWRCGSYCMB-UHFFFAOYSA-N hydron;piperazine;dichloride Chemical compound Cl.Cl.C1CNCCN1 CVVIJWRCGSYCMB-UHFFFAOYSA-N 0.000 description 5
- 230000036632 reaction speed Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 1
- 241000357437 Mola Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006198 deformylation Effects 0.000 description 1
- 238000006344 deformylation reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- ZQVBNUIFDLXAFI-UHFFFAOYSA-N piperazine;hydrate;dihydrochloride Chemical compound O.[Cl-].[Cl-].C1C[NH2+]CC[NH2+]1 ZQVBNUIFDLXAFI-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- KIUIOLPVWCNIRM-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine hydrochloride Chemical compound Cl.N1=CN=CC2=C1C=CC=N2 KIUIOLPVWCNIRM-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7408978A FR2264016B1 (en, 2012) | 1974-03-15 | 1974-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050538A true CA1050538A (en) | 1979-03-13 |
Family
ID=9136412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA222,322A Expired CA1050538A (en) | 1974-03-15 | 1975-03-14 | Pyrimidine derivatives |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS6053032B2 (en, 2012) |
| CA (1) | CA1050538A (en, 2012) |
| CH (1) | CH602726A5 (en, 2012) |
| CS (1) | CS191261B2 (en, 2012) |
| DD (1) | DD117881A5 (en, 2012) |
| DK (1) | DK149430C (en, 2012) |
| FR (1) | FR2264016B1 (en, 2012) |
| GB (1) | GB1482853A (en, 2012) |
| IN (1) | IN140837B (en, 2012) |
| NL (1) | NL184835C (en, 2012) |
| PL (1) | PL94508B1 (en, 2012) |
| RO (1) | RO67338A (en, 2012) |
| SE (1) | SE420096B (en, 2012) |
| YU (1) | YU39115B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3326118A1 (de) | 1982-08-02 | 1984-02-09 | Byk Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz | Pyridopyrimidintrione, verfahren zu ihrer herstellung, ihre verwendung und sie enthaltende arzneimittel |
| JPH05136541A (ja) * | 1991-11-11 | 1993-06-01 | Nippon Avionics Co Ltd | プリント配線板 |
-
1974
- 1974-03-15 FR FR7408978A patent/FR2264016B1/fr not_active Expired
-
1975
- 1975-02-25 DK DK72475A patent/DK149430C/da not_active IP Right Cessation
- 1975-03-10 IN IN462/CAL/1975A patent/IN140837B/en unknown
- 1975-03-12 RO RO7581613A patent/RO67338A/ro unknown
- 1975-03-12 PL PL1975178687A patent/PL94508B1/pl unknown
- 1975-03-13 GB GB10401/75A patent/GB1482853A/en not_active Expired
- 1975-03-13 CH CH321275A patent/CH602726A5/xx not_active IP Right Cessation
- 1975-03-13 YU YU00610/75A patent/YU39115B/xx unknown
- 1975-03-13 SE SE7502847A patent/SE420096B/xx not_active IP Right Cessation
- 1975-03-14 CS CS751748A patent/CS191261B2/cs unknown
- 1975-03-14 JP JP50030977A patent/JPS6053032B2/ja not_active Expired
- 1975-03-14 CA CA222,322A patent/CA1050538A/en not_active Expired
- 1975-03-17 NL NLAANVRAGE7503166,A patent/NL184835C/xx not_active IP Right Cessation
- 1975-03-17 DD DD184824A patent/DD117881A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2264016B1 (en, 2012) | 1978-06-16 |
| SE420096B (sv) | 1981-09-14 |
| RO67338A (ro) | 1980-01-15 |
| DK149430C (da) | 1986-11-17 |
| NL184835B (nl) | 1989-06-16 |
| IN140837B (en, 2012) | 1976-12-25 |
| NL184835C (nl) | 1989-11-16 |
| GB1482853A (en) | 1977-08-17 |
| CH602726A5 (en, 2012) | 1978-07-31 |
| DD117881A5 (en, 2012) | 1976-02-05 |
| NL7503166A (nl) | 1975-09-17 |
| CS191261B2 (en) | 1979-06-29 |
| PL94508B1 (pl) | 1977-08-31 |
| JPS50148384A (en, 2012) | 1975-11-27 |
| JPS6053032B2 (ja) | 1985-11-22 |
| YU61075A (en) | 1982-02-28 |
| SE7502847L (en, 2012) | 1975-09-16 |
| YU39115B (en) | 1984-06-30 |
| DK149430B (da) | 1986-06-09 |
| DK72475A (en, 2012) | 1975-09-16 |
| FR2264016A1 (en, 2012) | 1975-10-10 |
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