CH421115A - Verfahren zur Herstellung von neuen Sulfonamiden und von deren Salzen - Google Patents
Verfahren zur Herstellung von neuen Sulfonamiden und von deren SalzenInfo
- Publication number
- CH421115A CH421115A CH1171261A CH1171261A CH421115A CH 421115 A CH421115 A CH 421115A CH 1171261 A CH1171261 A CH 1171261A CH 1171261 A CH1171261 A CH 1171261A CH 421115 A CH421115 A CH 421115A
- Authority
- CH
- Switzerland
- Prior art keywords
- meaning
- interrupted
- general formula
- ring
- process according
- Prior art date
Links
- 229940124530 sulfonamide Drugs 0.000 title claims description 14
- 150000003456 sulfonamides Chemical class 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 10
- 150000003839 salts Chemical class 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 150000003230 pyrimidines Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000003458 sulfonic acid derivatives Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- KAHHAPNRIQLSFT-UHFFFAOYSA-N 5-methoxypyrimidin-2-amine Chemical compound COC1=CN=C(N)N=C1 KAHHAPNRIQLSFT-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- -1 sulfonamide derivatives of thiodiazole Chemical class 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- BNTQJJOKCJLPHC-UHFFFAOYSA-N n-(5-methoxypyrimidin-2-yl)-4-methylbenzenesulfonamide Chemical compound N1=CC(OC)=CN=C1NS(=O)(=O)C1=CC=C(C)C=C1 BNTQJJOKCJLPHC-UHFFFAOYSA-N 0.000 description 4
- CTRTZNUCBQNRCK-UHFFFAOYSA-N COC1=CN=C(NS(=O)(=O)CCC(C)C)N=C1 Chemical compound COC1=CN=C(NS(=O)(=O)CCC(C)C)N=C1 CTRTZNUCBQNRCK-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- NUZLGABXLZBLIZ-UHFFFAOYSA-N Cl.NC1=NC=C(C=N1)OC Chemical compound Cl.NC1=NC=C(C=N1)OC NUZLGABXLZBLIZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 229940100389 Sulfonylurea Drugs 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002169 ethanolamines Chemical class 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- WLSUNIXHBRXXFV-UHFFFAOYSA-N n-(5-methylpyrimidin-2-yl)benzenesulfonamide Chemical compound N1=CC(C)=CN=C1NS(=O)(=O)C1=CC=CC=C1 WLSUNIXHBRXXFV-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 231100000456 subacute toxicity Toxicity 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RSGBMGFQNOGIPC-UHFFFAOYSA-N (4-methylphenyl) thiohypochlorite Chemical compound CC1=CC=C(SCl)C=C1 RSGBMGFQNOGIPC-UHFFFAOYSA-N 0.000 description 1
- IEXYFTGJMMQUBN-UHFFFAOYSA-N 1-chlorosulfonyloxy-2-ethoxyethane Chemical compound CCOCCOS(Cl)(=O)=O IEXYFTGJMMQUBN-UHFFFAOYSA-N 0.000 description 1
- DHXWIWZOQIUPOL-UHFFFAOYSA-N 1-chlorosulfonyloxy-3-methylbutane Chemical compound CC(C)CCOS(Cl)(=O)=O DHXWIWZOQIUPOL-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- PITKZVSTELAQAI-UHFFFAOYSA-N 3-methylbutane-1-sulfinyl chloride Chemical compound CC(C)CCS(Cl)=O PITKZVSTELAQAI-UHFFFAOYSA-N 0.000 description 1
- CDGZBXSRVMXAMG-UHFFFAOYSA-N 3-methylbutyl thiohypochlorite Chemical compound CC(C)CCSCl CDGZBXSRVMXAMG-UHFFFAOYSA-N 0.000 description 1
- YTUTYZGQRFAXDA-UHFFFAOYSA-N 4-methyl-N-(5-propoxypyrimidin-2-yl)benzenesulfonamide Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC1=NC=C(C=N1)OCCC YTUTYZGQRFAXDA-UHFFFAOYSA-N 0.000 description 1
- DYYLCPSSSFWEEA-UHFFFAOYSA-N 4-methylbenzenesulfinyl chloride Chemical compound CC1=CC=C(S(Cl)=O)C=C1 DYYLCPSSSFWEEA-UHFFFAOYSA-N 0.000 description 1
- NGWGYIGTWBAKAN-UHFFFAOYSA-N 5-ethoxypyrimidin-2-amine Chemical compound CCOC1=CN=C(N)N=C1 NGWGYIGTWBAKAN-UHFFFAOYSA-N 0.000 description 1
- JCKHSOMIXYGMOX-UHFFFAOYSA-N 5-propoxypyrimidin-2-amine Chemical compound CCCOC1=CN=C(N)N=C1 JCKHSOMIXYGMOX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- YWJHQUXVKHTQSK-UHFFFAOYSA-N C(CC(C)C)SNC1=NC=C(C=N1)OC Chemical compound C(CC(C)C)SNC1=NC=C(C=N1)OC YWJHQUXVKHTQSK-UHFFFAOYSA-N 0.000 description 1
- YJIUIIUXSLOMCH-UHFFFAOYSA-N CC1=CC=C(C=C1)S(=O)NC1=NC=C(C=N1)OC Chemical compound CC1=CC=C(C=C1)S(=O)NC1=NC=C(C=N1)OC YJIUIIUXSLOMCH-UHFFFAOYSA-N 0.000 description 1
- XXGVJQFWQJPOFP-UHFFFAOYSA-N CCOC1=CN=C(NS(=O)(=O)CCC(C)C)N=C1 Chemical compound CCOC1=CN=C(NS(=O)(=O)CCC(C)C)N=C1 XXGVJQFWQJPOFP-UHFFFAOYSA-N 0.000 description 1
- UYELNPSYXOJSRU-UHFFFAOYSA-N CCOCCS(NC(N=C1)=NC=C1OC)(=O)=O Chemical compound CCOCCS(NC(N=C1)=NC=C1OC)(=O)=O UYELNPSYXOJSRU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KJRBUYSUVXGUHC-UHFFFAOYSA-N Cl.NCOC1=NC=CC=N1 Chemical compound Cl.NCOC1=NC=CC=N1 KJRBUYSUVXGUHC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- WVKXJJRAANJWFG-UHFFFAOYSA-N N-(5-cyclohexyloxypyrimidin-2-yl)benzenesulfonamide Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC1=NC=C(C=N1)OC1CCCCC1 WVKXJJRAANJWFG-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- ANVDYLHKNDBHCA-UHFFFAOYSA-N NC1=CC=C(C=C1)S(=O)(=O)NN1N=C(C=C1)SC(C)C Chemical compound NC1=CC=C(C=C1)S(=O)(=O)NN1N=C(C=C1)SC(C)C ANVDYLHKNDBHCA-UHFFFAOYSA-N 0.000 description 1
- ZBSQZROSYZVCNG-UHFFFAOYSA-N NC1=NC=C(C=N1)OC1CCCCC1 Chemical compound NC1=NC=C(C=N1)OC1CCCCC1 ZBSQZROSYZVCNG-UHFFFAOYSA-N 0.000 description 1
- 208000015906 Necrobiotic disease Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 206010019692 hepatic necrosis Diseases 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 231100000149 liver necrosis Toxicity 0.000 description 1
- JIUMYKGZGQSCRK-UHFFFAOYSA-N n-(5-methoxypyrimidin-2-yl)acetamide Chemical compound COC1=CN=C(NC(C)=O)N=C1 JIUMYKGZGQSCRK-UHFFFAOYSA-N 0.000 description 1
- QBHACRJLGYNGIF-UHFFFAOYSA-N n-(5-propoxypyrimidin-2-yl)benzenesulfonamide Chemical compound N1=CC(OCCC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QBHACRJLGYNGIF-UHFFFAOYSA-N 0.000 description 1
- PJURMBJCMOPSHW-UHFFFAOYSA-N n-[5-(2-methoxyethoxy)pyrimidin-2-yl]benzenesulfonamide;sodium Chemical compound [Na].N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 PJURMBJCMOPSHW-UHFFFAOYSA-N 0.000 description 1
- HLBLNLYCFFWMFF-UHFFFAOYSA-N n-pyrimidin-2-ylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=NC=CC=N1 HLBLNLYCFFWMFF-UHFFFAOYSA-N 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- BBDNZMUIQBRBJH-UHFFFAOYSA-N sulfurochloridic acid;toluene Chemical compound OS(Cl)(=O)=O.CC1=CC=CC=C1 BBDNZMUIQBRBJH-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
- C07D239/69—Benzenesulfonamido-pyrimidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC028634 | 1960-10-18 | ||
| DE1961SC029273 DE1445142B2 (de) | 1960-10-18 | 1961-02-22 | 2-(benzolsulfonamido)-5-methoxyaethoxy- pyrimidinderivate |
| DESCH29280A DE1175680B (de) | 1961-02-22 | 1961-02-23 | Verfahren zur Herstellung von 2-Sulfonamidopyrimidinderivaten |
| DESCH29319A DE1215161B (de) | 1961-02-22 | 1961-03-02 | Verfahren zur Herstellung von in 5-Stellung substituierten 2-Aminopyrimidinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH421115A true CH421115A (de) | 1966-09-30 |
Family
ID=27437403
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1171261A CH421115A (de) | 1960-10-18 | 1961-10-10 | Verfahren zur Herstellung von neuen Sulfonamiden und von deren Salzen |
| CH1003666A CH433344A (de) | 1960-10-18 | 1961-10-10 | Verfahren zur Herstellung von neuen 2-Aminopyrimidinen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1003666A CH433344A (de) | 1960-10-18 | 1961-10-10 | Verfahren zur Herstellung von neuen 2-Aminopyrimidinen |
Country Status (3)
| Country | Link |
|---|---|
| CH (2) | CH421115A (en:Method) |
| DK (4) | DK107097C (en:Method) |
| NL (1) | NL139314B (en:Method) |
-
1961
- 1961-10-10 CH CH1171261A patent/CH421115A/de unknown
- 1961-10-10 CH CH1003666A patent/CH433344A/de unknown
- 1961-10-13 DK DK345963A patent/DK107097C/da active
- 1961-10-13 DK DK407961A patent/DK106851C/da active
- 1961-10-13 DK DK345863A patent/DK106852C/da active
- 1961-10-13 DK DK346063A patent/DK106800C/da active
- 1961-10-18 NL NL61270346A patent/NL139314B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH433344A (de) | 1967-04-15 |
| NL270346A (en:Method) | |
| DK106800C (da) | 1967-03-20 |
| DK106851C (da) | 1967-03-28 |
| NL139314B (nl) | 1973-07-16 |
| DK106852C (da) | 1967-03-28 |
| DK107097C (da) | 1967-04-24 |
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