NO782340L - Fremgangsmaate for fremstilling av farmakologisk aktive benzylpyrimidiner - Google Patents

Fremgangsmaate for fremstilling av farmakologisk aktive benzylpyrimidiner

Info

Publication number: NO782340L
Authority: NO; Norway
Prior art keywords: general formula; compound; pyrimidine; trimethoxybenzyl; atoms
Prior art date: 1977-07-06

Application number

NO782340A

Other languages

English (en)

Norwegian (no)

Inventor

Klaus Gutsche

Peter Scharwaechter

Wilhelm Kohlmann

Gerhard Kroemer

Original Assignee

Basf Ag

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.)

1977-07-06

Filing date

1978-07-05

Publication date

1979-01-09

1978-07-05 Application filed by Basf Ag filed Critical Basf Ag

1979-01-09 Publication of NO782340L publication Critical patent/NO782340L/no

Links

238000002360 preparation method Methods 0.000 title claims description 7
238000000034 method Methods 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 16
-1 cyclic amine Chemical class 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
OOLOAWZLPBDRJQ-UHFFFAOYSA-N 2-benzylpyrimidine Chemical class N=1C=CC=NC=1CC1=CC=CC=C1 OOLOAWZLPBDRJQ-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000005037 alkyl phenyl group Chemical group 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1
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 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
229960001082 trimethoprim Drugs 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
150000003456 sulfonamides Chemical class 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
229940124530 sulfonamide Drugs 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000000243 solution Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
239000000203 mixture Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
IFLXPFPDRCASRC-UHFFFAOYSA-N 2-n-(cyclohexyloxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CC=2C(=NC(NCOC3CCCCC3)=NC=2)N)=C1 IFLXPFPDRCASRC-UHFFFAOYSA-N 0.000 description 2
IMPUXVGXZZPILE-UHFFFAOYSA-N 2-n-(methoxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.NC1=NC(NCOC)=NC=C1CC1=CC(OC)=C(OC)C(OC)=C1 IMPUXVGXZZPILE-UHFFFAOYSA-N 0.000 description 2
OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000193985 Streptococcus agalactiae Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
GYCLGFVWNVHUPA-UHFFFAOYSA-N chloromethoxycyclohexane Chemical compound ClCOC1CCCCC1 GYCLGFVWNVHUPA-UHFFFAOYSA-N 0.000 description 2
LADPCMZCENPFGV-UHFFFAOYSA-N chloromethoxymethylbenzene Chemical compound ClCOCC1=CC=CC=C1 LADPCMZCENPFGV-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229940127089 cytotoxic agent Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
239000000047 product Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000013558 reference substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
NEFNOUUWYACOKP-UHFFFAOYSA-N 1-(chloromethoxy)butane Chemical compound CCCCOCCl NEFNOUUWYACOKP-UHFFFAOYSA-N 0.000 description 1
AGDIDCDJVCRQCJ-UHFFFAOYSA-N 1-(chloromethoxy)hexane Chemical compound CCCCCCOCCl AGDIDCDJVCRQCJ-UHFFFAOYSA-N 0.000 description 1
VHUQXPJHMISKGS-UHFFFAOYSA-N 1-(chloromethoxy)propane Chemical compound CCCOCCl VHUQXPJHMISKGS-UHFFFAOYSA-N 0.000 description 1
QTCKZDZOQXBHHH-UHFFFAOYSA-N 1-chloro-2-(chloromethoxy)propane Chemical compound ClCC(C)OCCl QTCKZDZOQXBHHH-UHFFFAOYSA-N 0.000 description 1
JXXQSFUWEIFWJY-UHFFFAOYSA-N 2-(2-hydroxyethyl)guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(N)=NCCO JXXQSFUWEIFWJY-UHFFFAOYSA-N 0.000 description 1
DITIPOXEWUGULB-UHFFFAOYSA-N 2-(2-phenylethyl)guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(N)=NCCC1=CC=CC=C1 DITIPOXEWUGULB-UHFFFAOYSA-N 0.000 description 1
FQYRFGGSTJTBEJ-UHFFFAOYSA-N 2-(2-pyrrolidin-1-ylethyl)guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(N)=NCCN1CCCC1 FQYRFGGSTJTBEJ-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
GBPWFXAWLHBOCQ-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(N)=NCC1=CC=C(Cl)C=C1 GBPWFXAWLHBOCQ-UHFFFAOYSA-N 0.000 description 1
KBBNFTOXDUKKGX-UHFFFAOYSA-N 2-amino-n-(4,5-dimethyl-1,3-oxazol-2-yl)benzenesulfonamide Chemical compound O1C(C)=C(C)N=C1NS(=O)(=O)C1=CC=CC=C1N KBBNFTOXDUKKGX-UHFFFAOYSA-N 0.000 description 1
SQYPEJLKAOZVHW-UHFFFAOYSA-N 2-benzylguanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(N)=NCC1=CC=CC=C1.NC(N)=NCC1=CC=CC=C1 SQYPEJLKAOZVHW-UHFFFAOYSA-N 0.000 description 1
WZBYDPPOLTUYSM-UHFFFAOYSA-N 2-n-(1-chloropropan-2-yloxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CC=2C(=NC(NCOC(C)CCl)=NC=2)N)=C1 WZBYDPPOLTUYSM-UHFFFAOYSA-N 0.000 description 1
XNJYJCJFZWEAFJ-UHFFFAOYSA-N 2-n-(butoxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.NC1=NC(NCOCCCC)=NC=C1CC1=CC(OC)=C(OC)C(OC)=C1 XNJYJCJFZWEAFJ-UHFFFAOYSA-N 0.000 description 1
LLJUOMZFSBAYIW-UHFFFAOYSA-N 2-n-(cyclohexyloxymethyl)-5-[(4-methoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(C(=N1)N)=CN=C1NCOC1CCCCC1 LLJUOMZFSBAYIW-UHFFFAOYSA-N 0.000 description 1
XQMFKIMZKRKCSF-UHFFFAOYSA-N 2-n-(hexoxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.NC1=NC(NCOCCCCCC)=NC=C1CC1=CC(OC)=C(OC)C(OC)=C1 XQMFKIMZKRKCSF-UHFFFAOYSA-N 0.000 description 1
PJYHEIWNIDKXOQ-UHFFFAOYSA-N 2-n-(phenylmethoxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CC=2C(=NC(NCOCC=3C=CC=CC=3)=NC=2)N)=C1 PJYHEIWNIDKXOQ-UHFFFAOYSA-N 0.000 description 1
FKKKHYTUOJMSRF-UHFFFAOYSA-N 2-n-(propoxymethyl)-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.NC1=NC(NCOCCC)=NC=C1CC1=CC(OC)=C(OC)C(OC)=C1 FKKKHYTUOJMSRF-UHFFFAOYSA-N 0.000 description 1
ATOMBSOAMRAQHY-UHFFFAOYSA-N 2-n-[(4-chlorophenyl)methyl]-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(NCC=3C=CC(Cl)=CC=3)=NC=2)N)=C1 ATOMBSOAMRAQHY-UHFFFAOYSA-N 0.000 description 1
QGINLKLHYGYAFA-UHFFFAOYSA-N 2-n-benzyl-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(NCC=3C=CC=CC=3)=NC=2)N)=C1 QGINLKLHYGYAFA-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
WUEZQZHHXYEAQM-UHFFFAOYSA-N 2-prop-2-enylguanidine Chemical compound NC(N)=NCC=C WUEZQZHHXYEAQM-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
LINYIIJIYSUIET-UHFFFAOYSA-N 3-tert-butyl-5-(chloromethyl)-1,2-oxazole Chemical compound CC(C)(C)C=1C=C(CCl)ON=1 LINYIIJIYSUIET-UHFFFAOYSA-N 0.000 description 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
XIKYUFRCSIWOSF-UHFFFAOYSA-N 5-(chloromethyl)-3-ethyl-1,2-oxazole Chemical compound CCC=1C=C(CCl)ON=1 XIKYUFRCSIWOSF-UHFFFAOYSA-N 0.000 description 1
ZWBJJNWJUXXFNP-UHFFFAOYSA-N 5-(chloromethyl)-3-methyl-1,2-oxazole Chemical compound CC=1C=C(CCl)ON=1 ZWBJJNWJUXXFNP-UHFFFAOYSA-N 0.000 description 1
DXCHZEISFLMPFZ-UHFFFAOYSA-N 5-(chloromethyl)-3-propan-2-yl-1,2-oxazole Chemical compound CC(C)C=1C=C(CCl)ON=1 DXCHZEISFLMPFZ-UHFFFAOYSA-N 0.000 description 1
SAIIUKTXZZMVHR-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CC1=CC=CC=C1Cl SAIIUKTXZZMVHR-UHFFFAOYSA-N 0.000 description 1
BBLODNGDBRYXTB-UHFFFAOYSA-N 5-[(3,4-dimethoxyphenyl)methyl]-2-n-(phenylmethoxymethyl)pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CC(C(=N1)N)=CN=C1NCOCC1=CC=CC=C1 BBLODNGDBRYXTB-UHFFFAOYSA-N 0.000 description 1
KNMBSJCWXZMBIJ-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CC1=CC=C(Cl)C=C1 KNMBSJCWXZMBIJ-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
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208000005141 Otitis Diseases 0.000 description 1
206010040047 Sepsis Diseases 0.000 description 1
PJSFRIWCGOHTNF-UHFFFAOYSA-N Sulphormetoxin Chemical compound COC1=NC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1OC PJSFRIWCGOHTNF-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000005336 allyloxy group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
LDBTVAXGKYIFHO-UHFFFAOYSA-N diaveridine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=CN=C(N)N=C1N LDBTVAXGKYIFHO-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
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239000003623 enhancer Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
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230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000007941 film coated tablet Substances 0.000 description 1
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231100000636 lethal dose Toxicity 0.000 description 1
201000004792 malaria Diseases 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
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229910017604 nitric acid Inorganic materials 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
210000004798 organs belonging to the digestive system Anatomy 0.000 description 1
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239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
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230000009257 reactivity Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
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SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 description 1
KXRZBTAEDBELFD-UHFFFAOYSA-N sulfamethopyrazine Chemical compound COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 KXRZBTAEDBELFD-UHFFFAOYSA-N 0.000 description 1
GPTONYMQFTZPKC-UHFFFAOYSA-N sulfamethoxydiazine Chemical compound N1=CC(OC)=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 GPTONYMQFTZPKC-UHFFFAOYSA-N 0.000 description 1
VLYWMPOKSSWJAL-UHFFFAOYSA-N sulfamethoxypyridazine Chemical compound N1=NC(OC)=CC=C1NS(=O)(=O)C1=CC=C(N)C=C1 VLYWMPOKSSWJAL-UHFFFAOYSA-N 0.000 description 1
YZMCKZRAOLZXAZ-UHFFFAOYSA-N sulfisomidine Chemical compound CC1=NC(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 YZMCKZRAOLZXAZ-UHFFFAOYSA-N 0.000 description 1
JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
210000001635 urinary tract Anatomy 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO782340A 1977-07-06 1978-07-05 Fremgangsmaate for fremstilling av farmakologisk aktive benzylpyrimidiner NO782340L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772730467 DE2730467A1 (de)	1977-07-06	1977-07-06	Benzylpyrimidine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
NO782340L true NO782340L (no)	1979-01-09

Family

ID=6013252

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO782340A NO782340L (no)	1977-07-06	1978-07-05	Fremgangsmaate for fremstilling av farmakologisk aktive benzylpyrimidiner

Country Status (17)

Country	Link
US (1)	US4279899A (fr)
EP (1)	EP0000334B1 (fr)
JP (1)	JPS5416482A (fr)
AR (1)	AR223465A1 (fr)
AT (1)	AT361931B (fr)
AU (1)	AU515661B2 (fr)
CA (1)	CA1102324A (fr)
DE (2)	DE2730467A1 (fr)
DK (1)	DK142578C (fr)
FI (1)	FI782173A (fr)
HU (1)	HU179407B (fr)
IE (1)	IE781308L (fr)
IL (1)	IL55018A (fr)
IN (1)	IN149577B (fr)
IT (1)	IT7825220A0 (fr)
NO (1)	NO782340L (fr)
ZA (1)	ZA783873B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4438267A (en) *	1980-11-11	1984-03-20	Daluge Susan M	Monoheteroring compounds and their use
DE3045720A1 (de) *	1980-12-04	1982-07-08	Basf Ag, 6700 Ludwigshafen	N-pyrimidinyl-carbaminsaeureester, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
HU187370B (en) *	1981-06-26	1985-12-28	Egyt Gyogyszervegyeszeti Gyar	Improved process for producing 2,4-diamino-5-bracket-3-comma above, 4-comma above,5-comma above-trimethoxy-benzyl-bracket closed-pyrimidine
HU186413B (en) *	1981-06-26	1985-07-29	Egyt Gyogyszervegyeszeti Gyar	Process for producing 2,4-diamino-5-bracket-3-comma above,4-comma above,5-comma above-trimethoxy-benzyl-bracket closed-pyrimidine
JP4460292B2 (ja) *	2001-10-17	2010-05-12	ベーリンガーインゲルハイムファルマゲゼルシャフトミットベシュレンクテルハフツングウントコンパニーコマンディトゲゼルシャフト	ピリミジン誘導体、これらの化合物を含む医薬組成物、その使用及びその調製方法
AR081626A1 (es)	2010-04-23	2012-10-10	Cytokinetics Inc	Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos
AR081331A1 (es)	2010-04-23	2012-08-08	Cytokinetics Inc	Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos
EP2560488B1 (fr)	2010-04-23	2015-10-28	Cytokinetics, Inc.	Aminopyridines et aminotriazines, leurs compositions et leurs procédés d'utilisation

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3049544A (en) *		1962-08-14		Method for the preparation of
US2723975A (en) *	1952-04-03	1955-11-15	Nepera Chemical Co Inc	2, 4-di-piperidino-5-benzylpyrimidine
US2649449A (en) *	1952-04-04	1953-08-18	Nepera Chemical Co Inc	2-cyclohexylamino-4-amino-5-benzylpyrimidine
CH376115A (de) *	1957-12-06	1964-03-31	Ciba Geigy	Verfahren zur Herstellung neuer substituierter Pyrimidine
US3515783A (en)	1967-10-20	1970-06-02	Hoffmann La Roche	Antibacterial composition containing 5-methyl - 3 - sulfanilamidoisoxazole and trimethoxybenzyl pyrimidine
US4115650A (en) *	1976-11-17	1978-09-19	Hoffmann-La Roche Inc.	Process for preparing 2,4-diamino-5-(substituted benzyl)-pyrimidines

1977
- 1977-07-06 DE DE19772730467 patent/DE2730467A1/de not_active Withdrawn
1978
- 1978-06-16 EP EP78100180A patent/EP0000334B1/fr not_active Expired
- 1978-06-16 DE DE7878100180T patent/DE2860928D1/de not_active Expired
- 1978-06-27 US US05/919,505 patent/US4279899A/en not_active Expired - Lifetime
- 1978-06-27 IL IL55018A patent/IL55018A/xx unknown
- 1978-06-29 IE IE781308A patent/IE781308L/xx unknown
- 1978-06-30 AU AU37644/78A patent/AU515661B2/en not_active Expired
- 1978-06-30 IT IT7825220A patent/IT7825220A0/it unknown
- 1978-07-04 AR AR272831A patent/AR223465A1/es active
- 1978-07-04 CA CA306,732A patent/CA1102324A/fr not_active Expired
- 1978-07-04 HU HU78BA3672A patent/HU179407B/hu unknown
- 1978-07-05 NO NO782340A patent/NO782340L/no unknown
- 1978-07-05 FI FI782173A patent/FI782173A/fi not_active Application Discontinuation
- 1978-07-05 AT AT487478A patent/AT361931B/de not_active IP Right Cessation
- 1978-07-05 DK DK303178A patent/DK142578C/da active
- 1978-07-05 ZA ZA00783873A patent/ZA783873B/xx unknown
- 1978-07-06 JP JP8153078A patent/JPS5416482A/ja active Pending
- 1978-07-06 IN IN747/CAL/78A patent/IN149577B/en unknown

Also Published As

Publication number	Publication date
ZA783873B (en)	1979-08-29
AT361931B (de)	1981-04-10
FI782173A (fi)	1979-01-07
AR223465A1 (es)	1981-08-31
IL55018A (en)	1983-03-31
IN149577B (fr)	1982-01-30
ATA487478A (de)	1980-09-15
AU515661B2 (en)	1981-04-16
IT7825220A0 (it)	1978-06-30
JPS5416482A (en)	1979-02-07
US4279899A (en)	1981-07-21
AU3764478A (en)	1980-01-03
DK142578B (da)	1980-11-24
DE2860928D1 (en)	1981-11-12
HU179407B (en)	1982-10-28
CA1102324A (fr)	1981-06-02
DK142578C (da)	1981-07-20
IE781308L (en)	1979-01-06
EP0000334A1 (fr)	1979-01-24
DK303178A (da)	1979-01-07
EP0000334B1 (fr)	1981-08-12
IL55018A0 (en)	1978-08-31
DE2730467A1 (de)	1979-01-18

Publication	Publication Date	Title
EP0051879B1 (fr)	1986-02-05	Pyrimidines substituées, leur synthèse et compositions les contenant, leur usage en médecine et intermédiaires pour leur synthèse
DE69920509T2 (de)	2006-03-09	Pyrimidine verbindungen
JP2795498B2 (ja)	1998-09-10	薬理学的に活性な中枢神経系化合物
US3769286A (en)	1973-10-30	Trialkoxy quinazolines
RU2091374C1 (ru)	1997-09-27	Способ получения замещенных 5-арил-пиримидинов
US8536184B2 (en)	2013-09-17	Nitrogenous heterocyclic compounds and process for making nitrogenous heterocyclic compounds and intermediates thereof
CZ302136B6 (cs)	2010-11-10	Krystalické soli 7-{4-(4-fluorfenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl}-(3R,5S)-3,5-dihydroxyhept-6-enové kyseliny
CA2128917A1 (fr)	1995-02-14	Derives pyrimidine et pyridine, leur production et leur utilisation
US4515948A (en)	1985-05-07	2,4-Diamino-5-(4-amino and 4-dimethylamino-3,5-dimethoxy benzyl)pyrimidines
WO1995013267A1 (fr)	1995-05-18	Composes a base de pyrimidine-thioalkyle et d'alkylether
NO782340L (no)	1979-01-09	Fremgangsmaate for fremstilling av farmakologisk aktive benzylpyrimidiner
US7399760B2 (en)	2008-07-15	Pyrimidinedione derivatives
Ohno et al.	1986	Synthesis and Hypoglycemic Activity of 7, 8-Dihydro-6H-thiopyrano [3, 2-d] pyrimidine Derivatives and Related Compounds
US4590271A (en)	1986-05-20	2,4-diamino-5-(substituted)pyrimidines, useful as antimicrobials
SK125299A3 (en)	2001-12-03	Novel carboxylic acid derivatives, their preparation and use in treating cancer
EP0054756B1 (fr)	1986-07-23	Benzylpyrimidines antibactériennes
DE102004022672A1 (de)	2005-11-24	Substituierte Azachinazoline
KR820001338B1 (ko)	1982-07-28	벤질 피리미딘의 제조방법
US3553198A (en)	1971-01-05	2,4,6-substituted-5-arylsulfonyl-pyrimidines
NO782341L (no)	1979-01-09	Fremgangsmaate for fremstilling av farmakologisk aktive n-pyrimidinyl-imidsyreestere
JPH0559015A (ja)	1993-03-09	ピリミジン誘導体及び該誘導体を有効成分とする除草剤
US4333936A (en)	1982-06-08	Novel amidino-benzylpyrimidines, processes for their manufacture and antibacterial and antiprotozoal use thereof
JPS5973573A (ja)	1984-04-25	ジアミノピリミジン化合物
WO1990014340A1 (fr)	1990-11-29	Derives d'acide glutamique