CS212733B2 - Způsob výroby 2,4-diandno-5-benzylpyriml(Jinových derivátů - Google Patents

Způsob výroby 2,4-diandno-5-benzylpyriml(Jinových derivátů Download PDF

Info

Publication number: CS212733B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; diamino; acid; hydrogen; alkyl
Prior art date: 1971-10-12

Application number

CS683672A

Other languages

Czech (cs)

English (en)

Inventor

Alexander Stuart

Thomas Paterson

Original Assignee

Alexander Stuart

Thomas Paterson

Priority date (The priority date 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 date listed.)

1971-10-12

Filing date

1972-10-10

Publication date

1982-03-26

1971-10-12 Priority claimed from GB4749271A external-priority patent/GB1413471A/en

1972-10-10 Application filed by Alexander Stuart, Thomas Paterson filed Critical Alexander Stuart

1982-03-26 Publication of CS212733B2 publication Critical patent/CS212733B2/cs

Links

238000000034 method Methods 0.000 title claims description 26
XHPZVBGIPQQTQW-UHFFFAOYSA-N 5-benzylpyrimidine-2,4-diamine Chemical class NC1=NC(N)=NC=C1CC1=CC=CC=C1 XHPZVBGIPQQTQW-UHFFFAOYSA-N 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 9
150000002989 phenols Chemical class 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
-1 2,4-diaminopyrimidin-5-ylmethyl group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
239000003377 acid catalyst Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229940100198 alkylating agent Drugs 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
150000001735 carboxylic acids Chemical class 0.000 claims description 3
239000002798 polar solvent Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
235000014113 dietary fatty acids Nutrition 0.000 claims 1
229930195729 fatty acid Natural products 0.000 claims 1
239000000194 fatty acid Substances 0.000 claims 1
150000004665 fatty acids Chemical class 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
150000007522 mineralic acids Chemical class 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
230000008018 melting Effects 0.000 description 8
238000002844 melting Methods 0.000 description 8
METWAQRCMRWDAW-UHFFFAOYSA-N 2,6-diethylphenol Chemical compound CCC1=CC=CC(CC)=C1O METWAQRCMRWDAW-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
239000000047 product Substances 0.000 description 7
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
MMDZZHAZMNJFMW-UHFFFAOYSA-N (2,4-diaminopyrimidin-5-yl)methanol Chemical compound NC1=NC=C(CO)C(N)=N1 MMDZZHAZMNJFMW-UHFFFAOYSA-N 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
KLAQSPUVCDBEGF-UHFFFAOYSA-N 2,3,5,6-tetramethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1C KLAQSPUVCDBEGF-UHFFFAOYSA-N 0.000 description 4
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
OYUQCQCQLDTRHQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbonitrile Chemical compound NC1=NC=C(C#N)C(N)=N1 OYUQCQCQLDTRHQ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000002585 base Substances 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
230000011987 methylation Effects 0.000 description 3
238000007069 methylation reaction Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
VGXYFEJQMPXSER-UHFFFAOYSA-N 4-(pyrimidin-2-ylmethyl)phenol Chemical class C1=CC(O)=CC=C1CC1=NC=CC=N1 VGXYFEJQMPXSER-UHFFFAOYSA-N 0.000 description 2
WIYWMZNHABWRHH-UHFFFAOYSA-N 4-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3,5,6-tetramethylphenol Chemical compound CC1=C(O)C(C)=C(C)C(CC=2C(=NC(N)=NC=2)N)=C1C WIYWMZNHABWRHH-UHFFFAOYSA-N 0.000 description 2
HPOCGNHBIFZCAN-UHFFFAOYSA-N 4-[(2,4-diaminopyrimidin-5-yl)methyl]-2,6-dimethoxyphenol Chemical compound COC1=C(O)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 HPOCGNHBIFZCAN-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
230000000078 anti-malarial effect Effects 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
TYRDEZUMAVRTEO-UHFFFAOYSA-N pyrimidin-5-ylmethanol Chemical compound OCC1=CN=CN=C1 TYRDEZUMAVRTEO-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
PWROXEYGGQKRSI-UHFFFAOYSA-N 2-[(2,4-diaminopyrimidin-5-yl)methyl]-4,6-dimethylphenol Chemical compound CC1=CC(C)=C(O)C(CC=2C(=NC(N)=NC=2)N)=C1 PWROXEYGGQKRSI-UHFFFAOYSA-N 0.000 description 1
DGKZRBYZZOWQFM-UHFFFAOYSA-N 2-benzyl-1h-pyrimidin-6-one Chemical class N1C(=O)C=CN=C1CC1=CC=CC=C1 DGKZRBYZZOWQFM-UHFFFAOYSA-N 0.000 description 1
OOLOAWZLPBDRJQ-UHFFFAOYSA-N 2-benzylpyrimidine Chemical class N=1C=CC=NC=1CC1=CC=CC=C1 OOLOAWZLPBDRJQ-UHFFFAOYSA-N 0.000 description 1
XQOVESDGYWUUTD-UHFFFAOYSA-N 3-[(2,4-diaminopyrimidin-5-yl)methyl]-2,6-dimethoxyphenol Chemical compound COC1=C(O)C(OC)=CC=C1CC1=CN=C(N)N=C1N XQOVESDGYWUUTD-UHFFFAOYSA-N 0.000 description 1
YZDAHKBHIGEAAB-UHFFFAOYSA-N 4-[(2,4-diaminopyrimidin-5-yl)methyl]-2,6-di(propan-2-yl)phenol Chemical compound CC(C)C1=C(O)C(C(C)C)=CC(CC=2C(=NC(N)=NC=2)N)=C1 YZDAHKBHIGEAAB-UHFFFAOYSA-N 0.000 description 1
VUYZAOCZFHLOER-UHFFFAOYSA-N 4-[(2,4-diaminopyrimidin-5-yl)methyl]-2,6-diethylphenol Chemical compound CCC1=C(O)C(CC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 VUYZAOCZFHLOER-UHFFFAOYSA-N 0.000 description 1
JWSXYKJRCWICKV-UHFFFAOYSA-N 4-[(2,4-diaminopyrimidin-5-yl)methyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CC=2C(=NC(N)=NC=2)N)=C1 JWSXYKJRCWICKV-UHFFFAOYSA-N 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 1
UESKVZGVVYLDTG-UHFFFAOYSA-N 5-(bromomethyl)pyrimidine-2,4-diamine Chemical compound NC1=NC=C(CBr)C(N)=N1 UESKVZGVVYLDTG-UHFFFAOYSA-N 0.000 description 1
LMDWIFOXRXQEPO-UHFFFAOYSA-N 5-[(2,3,4-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound COC1=C(OC)C(OC)=CC=C1CC1=CN=C(N)N=C1N LMDWIFOXRXQEPO-UHFFFAOYSA-N 0.000 description 1
NHRWIXKBNBUJLF-UHFFFAOYSA-N 5-[(2-methoxy-3,5-dimethylphenyl)methyl]pyrimidine-2,4-diamine Chemical compound COC1=C(C)C=C(C)C=C1CC1=CN=C(N)N=C1N NHRWIXKBNBUJLF-UHFFFAOYSA-N 0.000 description 1
OMMIPZRITGPWHK-UHFFFAOYSA-N 5-[(4-ethoxy-2,3,5,6-tetramethylphenyl)methyl]pyrimidine-2,4-diamine Chemical compound CC1=C(C)C(OCC)=C(C)C(C)=C1CC1=CN=C(N)N=C1N OMMIPZRITGPWHK-UHFFFAOYSA-N 0.000 description 1
DOUDCSREUZJYFB-UHFFFAOYSA-N 5-[(4-methoxy-3,5-dimethylphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(C)C(OC)=C(C)C=C1CC1=CN=C(N)N=C1N DOUDCSREUZJYFB-UHFFFAOYSA-N 0.000 description 1
RNWMSFXMEDHASR-UHFFFAOYSA-N 5-benzylpyridine-2,4-diamine Chemical class C1=NC(N)=CC(N)=C1CC1=CC=CC=C1 RNWMSFXMEDHASR-UHFFFAOYSA-N 0.000 description 1
229910000838 Al alloy Inorganic materials 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 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
229910000990 Ni alloy Inorganic materials 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000003430 antimalarial agent Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Substances CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229960001867 guaiacol Drugs 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
125000006289 hydroxybenzyl group Chemical group 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000003335 steric effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1

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Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS683672A 1971-10-12 1972-10-10 Způsob výroby 2,4-diandno-5-benzylpyriml(Jinových derivátů CS212733B2 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB4749271A GB1413471A (en)	1971-10-12	1971-10-12	2,4-diamino-5-benzylpyrimidines and a process for their preparation

Publications (1)

Publication Number	Publication Date
CS212733B2 true CS212733B2 (cs)	1982-03-26

Family

ID=10445183

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS683672A CS212733B2 (cs)	1971-10-12	1972-10-10	Způsob výroby 2,4-diandno-5-benzylpyriml(Jinových derivátů

Country Status (4)

Country	Link
AT (1)	AT336020B (de)
CS (1)	CS212733B2 (de)
HU (1)	HU169422B (de)
ZA (1)	ZA727250B (de)

1972
- 1972-10-10 CS CS683672A patent/CS212733B2/cs unknown
- 1972-10-10 AT AT868072A patent/AT336020B/de not_active IP Right Cessation
- 1972-10-11 ZA ZA727250A patent/ZA727250B/xx unknown
- 1972-10-12 HU HUWE000470 patent/HU169422B/hu unknown

Also Published As

Publication number	Publication date
HU169422B (de)	1976-11-28
ZA727250B (en)	1974-05-29
AT336020B (de)	1977-04-12
ATA868072A (de)	1976-08-15

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PL84115B3 (en)	1976-03-31	2-(furfuryl-methyl)-6,7-benzomorphans and acid addition salts thereof[us3823150a]
BR112021014815A2 (pt)	2021-09-28	Método para preparação de 4-amino-5-metilpiridona
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US6545149B2 (en)	2003-04-08	Synthesis and crystallization of piperazine ring-containing compounds
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