DE1114197B - Verfahren zur Herstellung von quaternierten 2-Mercapto-4-aminopyrimidinverbindungen - Google Patents
Verfahren zur Herstellung von quaternierten 2-Mercapto-4-aminopyrimidinverbindungenInfo
- Publication number
- DE1114197B DE1114197B DEF28236A DEF0028236A DE1114197B DE 1114197 B DE1114197 B DE 1114197B DE F28236 A DEF28236 A DE F28236A DE F0028236 A DEF0028236 A DE F0028236A DE 1114197 B DE1114197 B DE 1114197B
- Authority
- DE
- Germany
- Prior art keywords
- quaternized
- compounds
- denotes
- general formula
- mercapto
- 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 description 3
- 238000002360 preparation method Methods 0.000 title description 3
- DCPSTSVLRXOYGS-UHFFFAOYSA-N 6-amino-1h-pyrimidine-2-thione Chemical class NC1=CC=NC(S)=N1 DCPSTSVLRXOYGS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001302 tertiary amino group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- -1 aralkyl mercaptopyrimidine derivatives Chemical class 0.000 description 4
- 230000001085 cytostatic effect Effects 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical compound I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 201000009030 Carcinoma Diseases 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XMVNOXQZPHZCTQ-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylsulfanyl]-n,n,5-trimethylpyrimidin-4-amine Chemical compound C1=C(C)C(N(C)C)=NC(SCC=2C(=CC=CC=2)Cl)=N1 XMVNOXQZPHZCTQ-UHFFFAOYSA-N 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LQQXDTDDEYSIIA-UHFFFAOYSA-N C(C1=CC=CC=C1)SC1=NC(=CC(=N1)N(C)C)C Chemical compound C(C1=CC=CC=C1)SC1=NC(=CC(=N1)N(C)C)C LQQXDTDDEYSIIA-UHFFFAOYSA-N 0.000 description 1
- OOXGDALQWCHWAQ-UHFFFAOYSA-N C(C1=CC=CC=C1)SC1=NC(=NC(=C1)C)NCCCC Chemical compound C(C1=CC=CC=C1)SC1=NC(=NC(=C1)C)NCCCC OOXGDALQWCHWAQ-UHFFFAOYSA-N 0.000 description 1
- BTUPIZWOAYJBJO-UHFFFAOYSA-N ClC1=C(CSC2=NC(=CC(=N2)N2CCCCC2)C)C=CC=C1 Chemical compound ClC1=C(CSC2=NC(=CC(=N2)N2CCCCC2)C)C=CC=C1 BTUPIZWOAYJBJO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000009916 Yoshida Sarcoma Diseases 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF28236A DE1114197B (de) | 1959-04-17 | 1959-04-17 | Verfahren zur Herstellung von quaternierten 2-Mercapto-4-aminopyrimidinverbindungen |
FR837168A FR457M (enrdf_load_html_response) | 1959-04-17 | 1960-08-30 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF28236A DE1114197B (de) | 1959-04-17 | 1959-04-17 | Verfahren zur Herstellung von quaternierten 2-Mercapto-4-aminopyrimidinverbindungen |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1114197B true DE1114197B (de) | 1961-09-28 |
Family
ID=7092790
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF28236A Pending DE1114197B (de) | 1959-04-17 | 1959-04-17 | Verfahren zur Herstellung von quaternierten 2-Mercapto-4-aminopyrimidinverbindungen |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE1114197B (enrdf_load_html_response) |
FR (1) | FR457M (enrdf_load_html_response) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB658602A (en) * | 1948-08-24 | 1951-10-10 | Vickers Electrical Co Ltd | Improvements in operating mechanism for quick make and break electric switches |
DE823452B (de) | 1949-03-18 | 1951-10-25 | Imperial Chemical Industries Limited, London | Verfahren zur Herstellung von neuen quartären Salzen von Pyrimidinderivaten |
DE1023465B (de) | 1955-07-05 | 1958-01-30 | Bayer Ag | Verfahren zur Herstellung von Thiopyrimidinverbindungen |
-
1959
- 1959-04-17 DE DEF28236A patent/DE1114197B/de active Pending
-
1960
- 1960-08-30 FR FR837168A patent/FR457M/fr active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB658602A (en) * | 1948-08-24 | 1951-10-10 | Vickers Electrical Co Ltd | Improvements in operating mechanism for quick make and break electric switches |
DE823452B (de) | 1949-03-18 | 1951-10-25 | Imperial Chemical Industries Limited, London | Verfahren zur Herstellung von neuen quartären Salzen von Pyrimidinderivaten |
DE1023465B (de) | 1955-07-05 | 1958-01-30 | Bayer Ag | Verfahren zur Herstellung von Thiopyrimidinverbindungen |
Also Published As
Publication number | Publication date |
---|---|
FR457M (enrdf_load_html_response) | 1961-04-24 |
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