NO782341L - Fremgangsmaate for fremstilling av farmakologisk aktive n-pyrimidinyl-imidsyreestere - Google Patents

Fremgangsmaate for fremstilling av farmakologisk aktive n-pyrimidinyl-imidsyreestere

Info

Publication number: NO782341L
Authority: NO; Norway
Prior art keywords: methoxy; ethyl; hydrogen; pyrimidin; amino
Prior art date: 1977-07-06

Application number

NO782341A

Other languages

English (en)

Norwegian (no)

Inventor

Peter Scharwaechter

Klaus Gutsche

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 NO782341L publication Critical patent/NO782341L/no

Links

238000000034 method Methods 0.000 title claims abstract description 15
238000002360 preparation method Methods 0.000 title claims abstract description 8
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
150000002431 hydrogen Chemical class 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
238000004519 manufacturing process Methods 0.000 claims description 13
239000007858 starting material Substances 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 8
-1 N-[4-amino-5-(3,4,5-trimethoxybenzyl)-pyrimidin-2-yl]-butyrimidic acid ethyl ester Chemical compound 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
XAEXEPVKHZFXPC-UHFFFAOYSA-N ethyl N-[4-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-2-yl]ethanimidate Chemical compound C(C)OC(C)=NC1=NC(=C(C(=N1)N)C1=CC=C(C=C1)Cl)CC XAEXEPVKHZFXPC-UHFFFAOYSA-N 0.000 claims description 2
SZQPEQWJSHHWNX-UHFFFAOYSA-N ethyl N-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]-2-methylpropanimidate Chemical compound C(C)OC(C(C)C)=NC1=NC=C(C(=N1)N)CC1=CC(=C(C(=C1)OC)OC)OC SZQPEQWJSHHWNX-UHFFFAOYSA-N 0.000 claims description 2
QHACXHKLEYMANN-UHFFFAOYSA-N ethyl N-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]ethanimidate Chemical compound C(C)OC(C)=NC1=NC=C(C(=N1)N)CC1=CC(=C(C(=C1)OC)OC)OC QHACXHKLEYMANN-UHFFFAOYSA-N 0.000 claims description 2
ZPYLFXDWHKTTTN-UHFFFAOYSA-N ethyl N-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]propanimidate Chemical compound C(C)OC(CC)=NC1=NC=C(C(=N1)N)CC1=CC(=C(C(=C1)OC)OC)OC ZPYLFXDWHKTTTN-UHFFFAOYSA-N 0.000 claims description 2
HLUTYBKXXUTNEY-UHFFFAOYSA-N ethyl N-[4-amino-5-[(4-methoxyphenyl)methyl]pyrimidin-2-yl]ethanimidate Chemical compound C(C)OC(C)=NC1=NC=C(C(=N1)N)CC1=CC=C(C=C1)OC HLUTYBKXXUTNEY-UHFFFAOYSA-N 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
150000004702 methyl esters Chemical class 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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 14
NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
229960001082 trimethoprim Drugs 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 6
229940124530 sulfonamide Drugs 0.000 description 5
150000003456 sulfonamides Chemical class 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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 3
241001465754 Metazoa Species 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
239000000203 mixture Substances 0.000 description 3
FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 2
HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 2
241000193985 Streptococcus agalactiae Species 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
229940127089 cytotoxic agent Drugs 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002463 imidates Chemical class 0.000 description 2
239000013558 reference substance Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
KOPMZTKUZCNGFY-UHFFFAOYSA-N 1,1,1-triethoxybutane Chemical compound CCCC(OCC)(OCC)OCC KOPMZTKUZCNGFY-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OPMKWMZUBTUNEX-UHFFFAOYSA-N 2-amino-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC=CC=2)N)=N1 OPMKWMZUBTUNEX-UHFFFAOYSA-N 0.000 description 1
MTRRRDFGNMVWQW-UHFFFAOYSA-N 2-amino-n-(5-methylpyrimidin-2-yl)benzenesulfonamide Chemical compound N1=CC(C)=CN=C1NS(=O)(=O)C1=CC=CC=C1N MTRRRDFGNMVWQW-UHFFFAOYSA-N 0.000 description 1
CWSYFKKTOAFUJX-UHFFFAOYSA-N 3-amino-n-(2-phenylpyrazol-3-yl)benzenesulfonamide Chemical compound NC1=CC=CC(S(=O)(=O)NC=2N(N=CC=2)C=2C=CC=CC=2)=C1 CWSYFKKTOAFUJX-UHFFFAOYSA-N 0.000 description 1
XPGJOCWCEGOGMR-UHFFFAOYSA-N 3-amino-n-(6-chloropyridazin-3-yl)benzenesulfonamide Chemical compound NC1=CC=CC(S(=O)(=O)NC=2N=NC(Cl)=CC=2)=C1 XPGJOCWCEGOGMR-UHFFFAOYSA-N 0.000 description 1
CKKVFDQYOWXYQH-UHFFFAOYSA-N 5-[(2,4-dichlorophenyl)methyl]pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CC1=CC=C(Cl)C=C1Cl CKKVFDQYOWXYQH-UHFFFAOYSA-N 0.000 description 1
YFXPEDMBLISFPG-UHFFFAOYSA-N 5-[(3,4-dichlorophenyl)methyl]pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CC1=CC=C(Cl)C(Cl)=C1 YFXPEDMBLISFPG-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
YMGUVTBVYOGUFZ-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=CC(OC)=CC=C1CC1=CN=C(N)N=C1N YMGUVTBVYOGUFZ-UHFFFAOYSA-N 0.000 description 1
ZGWAEUUYBLJLPE-UHFFFAOYSA-N 5-[(4-methylphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=CC(C)=CC=C1CC1=CN=C(N)N=C1N ZGWAEUUYBLJLPE-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
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
239000013543 active substance Substances 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000001816 cooling Methods 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
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
208000019258 ear infection Diseases 0.000 description 1
CZRMBBRECCVWBQ-UHFFFAOYSA-N ethyl N-[4-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-2-yl]-2-phenylethanimidate Chemical compound C(C)OC(CC1=CC=CC=C1)=NC1=NC(=C(C(=N1)N)C1=CC=C(C=C1)Cl)CC CZRMBBRECCVWBQ-UHFFFAOYSA-N 0.000 description 1
ZYBLUYXQJHLOPR-UHFFFAOYSA-N ethyl N-[4-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-2-yl]propanimidate Chemical compound C(C)OC(CC)=NC1=NC(=C(C(=N1)N)C1=CC=C(C=C1)Cl)CC ZYBLUYXQJHLOPR-UHFFFAOYSA-N 0.000 description 1
JMHJAYHRTQYXTC-UHFFFAOYSA-N ethyl N-[4-amino-5-[(2,4-dichlorophenyl)methyl]pyrimidin-2-yl]ethanimidate Chemical compound C(C)OC(C)=NC1=NC=C(C(=N1)N)CC1=C(C=C(C=C1)Cl)Cl JMHJAYHRTQYXTC-UHFFFAOYSA-N 0.000 description 1
FRAOBKLFMTWRNA-UHFFFAOYSA-N ethyl N-[4-amino-5-[(4-chlorophenyl)methyl]pyrimidin-2-yl]ethanimidate Chemical compound C(C)OC(C)=NC1=NC=C(C(=N1)N)CC1=CC=C(C=C1)Cl FRAOBKLFMTWRNA-UHFFFAOYSA-N 0.000 description 1
LIELPDLLCQTTAC-UHFFFAOYSA-N ethyl N-[4-amino-5-[(4-methylphenyl)methyl]pyrimidin-2-yl]ethanimidate Chemical compound C(C)OC(C)=NC1=NC=C(C(=N1)N)CC1=CC=C(C=C1)C LIELPDLLCQTTAC-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000007941 film coated tablet Substances 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
201000004792 malaria Diseases 0.000 description 1
238000002156 mixing Methods 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
210000004798 organs belonging to the digestive system Anatomy 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
229960000611 pyrimethamine Drugs 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
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
BRBKOPJOKNSWSG-UHFFFAOYSA-N sulfaguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1 BRBKOPJOKNSWSG-UHFFFAOYSA-N 0.000 description 1
229960004257 sulfaguanidine Drugs 0.000 description 1
QPPBRPIAZZHUNT-UHFFFAOYSA-N sulfamerazine Chemical compound CC1=CC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 QPPBRPIAZZHUNT-UHFFFAOYSA-N 0.000 description 1
ASWVTGNCAZCNNR-UHFFFAOYSA-N sulfamethazine Chemical compound CC1=CC(C)=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ASWVTGNCAZCNNR-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
IZOYMGQQVNAMHS-UHFFFAOYSA-N sulfametrole Chemical compound COC1=NSN=C1NS(=O)(=O)C1=CC=C(N)C=C1 IZOYMGQQVNAMHS-UHFFFAOYSA-N 0.000 description 1
GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 description 1
JNMRHUJNCSQMMB-UHFFFAOYSA-N sulfathiazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-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
239000000725 suspension Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-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
- 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
- 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

Landscapes

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

NO782341A 1977-07-06 1978-07-05 Fremgangsmaate for fremstilling av farmakologisk aktive n-pyrimidinyl-imidsyreestere NO782341L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772730468 DE2730468A1 (de)	1977-07-06	1977-07-06	Neue n-pyrimidinyl-imidsaeureester, verfahren zu ihrer herstellung und diese enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
NO782341L true NO782341L (no)	1979-01-09

Family

ID=6013253

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO782341A NO782341L (no)	1977-07-06	1978-07-05	Fremgangsmaate for fremstilling av farmakologisk aktive n-pyrimidinyl-imidsyreestere

Country Status (15)

Country	Link
US (1)	US4315931A (de)
EP (1)	EP0000335B1 (de)
JP (1)	JPS5416483A (de)
AR (1)	AR220139A1 (de)
AT (1)	AT360998B (de)
AU (1)	AU515679B2 (de)
CA (1)	CA1107733A (de)
DE (2)	DE2730468A1 (de)
DK (1)	DK142577C (de)
FI (1)	FI782174A7 (de)
HU (1)	HU178177B (de)
IE (1)	IE47013B1 (de)
IL (1)	IL55020A (de)
NO (1)	NO782341L (de)
ZA (1)	ZA783874B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3045720A1 (de) *	1980-12-04	1982-07-08	Basf Ag, 6700 Ludwigshafen	N-pyrimidinyl-carbaminsaeureester, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
US4767443A (en) *	1984-09-20	1988-08-30	Ciba-Geigy Corporation	Antifungal and antibacterial diazine derivatives compositions, intermediates, and method of use therefor
CH668969A5 (de) *	1986-09-05	1989-02-15	Ciba Geigy Ag	Verfahren zur bekaempfung unerwuenschten pflanzenwuchses sowie zur regulierung des pflanzenwachstums.

Family Cites Families (2)

* 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
DE2732029A1 (de) *	1977-07-15	1979-02-01	Basf Ag	Neue amidino-benzylpyrimidine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel

1977
- 1977-07-06 DE DE19772730468 patent/DE2730468A1/de not_active Withdrawn
1978
- 1978-06-05 FI FI782174A patent/FI782174A7/fi not_active Application Discontinuation
- 1978-06-19 DE DE7878100183T patent/DE2861128D1/de not_active Expired
- 1978-06-19 EP EP78100183A patent/EP0000335B1/de not_active Expired
- 1978-06-27 IL IL55020A patent/IL55020A/xx unknown
- 1978-06-28 IE IE1292/78A patent/IE47013B1/en unknown
- 1978-06-30 AU AU37643/78A patent/AU515679B2/en not_active Expired
- 1978-07-03 US US06/921,701 patent/US4315931A/en not_active Expired - Lifetime
- 1978-07-04 AR AR272832A patent/AR220139A1/es active
- 1978-07-04 HU HU78BA3671A patent/HU178177B/hu unknown
- 1978-07-05 CA CA306,847A patent/CA1107733A/en not_active Expired
- 1978-07-05 AT AT487678A patent/AT360998B/de not_active IP Right Cessation
- 1978-07-05 ZA ZA00783874A patent/ZA783874B/xx unknown
- 1978-07-05 NO NO782341A patent/NO782341L/no unknown
- 1978-07-05 DK DK303278A patent/DK142577C/da active
- 1978-07-06 JP JP8153178A patent/JPS5416483A/ja active Pending

Also Published As

Publication number	Publication date
AR220139A1 (es)	1980-10-15
IE47013B1 (en)	1983-11-30
AU515679B2 (en)	1981-04-16
EP0000335B1 (de)	1981-10-07
FI782174A7 (fi)	1979-01-07
AU3764378A (en)	1980-01-03
DE2730468A1 (de)	1979-01-18
IL55020A (en)	1981-11-30
US4315931A (en)	1982-02-16
IE781292L (en)	1979-01-06
DE2861128D1 (en)	1981-12-17
EP0000335A1 (de)	1979-01-24
DK142577C (da)	1981-07-20
AT360998B (de)	1981-02-10
JPS5416483A (en)	1979-02-07
ATA487678A (de)	1980-07-15
ZA783874B (en)	1979-08-29
HU178177B (en)	1982-03-28
IL55020A0 (en)	1978-08-31
DK142577B (da)	1980-11-24
DK303278A (da)	1979-01-07
CA1107733A (en)	1981-08-25

Publication	Publication Date	Title
KR880001736B1 (ko)	1988-09-10	2,4-디아미노-5(치환된)피리미딘의 제조방법
DE60128343T2 (de)	2008-01-17	Pyrimidine verbindungen
DE60126071T2 (de)	2007-07-12	2,4-di(hetero-)arylamino(-oxy)-5-substituierte pyrimidinderivate als antineoplastika
US10590145B2 (en)	2020-03-17	Tetrahydrothiopyranopyrimidine derivatives as anti-HIV agent
DE102005062742A1 (de)	2007-06-28	Sulfoximin substituierte Pyrimidine, Verfahren zu deren Herstellung und ihre Verwendung als Arzneimittel
WO2005037800A1 (de)	2005-04-28	Sulfoximinsubstituierte pyrimidine als cdk- und/oder vegf-inhibitoren, deren herstellung und verwendung als arzneimittel
US11447501B2 (en)	2022-09-20	Biphenyl-containing diarylpyrimido compounds, pharmaceutically-acceptable salts thereof, composition and preparation thereof
Falco et al.	1951	2, 4-Diaminopyrimidines as Antimalarials. I. 1 5-Aryloxyl and 5-Alkoxyl Derivatives
US5151427A (en)	1992-09-29	Anthelminitics
EP2054053A1 (de)	2009-05-06	Biphenyl substituierte spirotetronsäuren und ihre verwendung zur behandlung retroviraler erkrankungen
NO782341L (no)	1979-01-09	Fremgangsmaate for fremstilling av farmakologisk aktive n-pyrimidinyl-imidsyreestere
US4189581A (en)	1980-02-19	2-Acylamino-4-amino-5-(3,4,5-trimethoxybenzyl)-pyrimidines
NO782340L (no)	1979-01-09	Fremgangsmaate for fremstilling av farmakologisk aktive benzylpyrimidiner
DE102012016908A1 (de)	2014-02-20	Tris-(Hetero)Aryl-Pyrazole und ihre Verwendung
NO782455L (no)	1979-01-16	Fremgangsmaate for fremstilling av farmakologisk aktive amidino-benzylpyrimidiner
KR820001321B1 (ko)	1982-07-23	N-피리미디닐-이미도산 에스테르의 제조방법
NO814138L (no)	1982-06-07	Analogifremgangsmaate for fremstilling av terapeutisk aktive n-pyrimidyl-karbaminsyreestere
US7371758B2 (en)	2008-05-13	Antimalarial pyrimidine derivatives and methods of making and using them
NO161102B (no)	1989-03-28	Lokkemat for gnagere omfattende foede og en gift.
US4333936A (en)	1982-06-08	Novel amidino-benzylpyrimidines, processes for their manufacture and antibacterial and antiprotozoal use thereof
SU1558915A1 (ru)	1990-04-23	2-(5 @ -Нитрофурил)-2,3-дигидро-5Н-1,3,4-тиадиазоло[2,3-в]-хиназолинон-5, про вл ющий противомикробную активность
US3787409A (en)	1974-01-22	2,4-diamino-5-(3-alkoxy-4,5-methylenedioxybenzyl)pyrimidine
US4073786A (en)	1978-02-14	2-Amino-4-hydroxy-6-hydroxymethyl-7,7-diethyl-7,8-dihydropteridine and the 7-spirocyclohexyl analogue thereof
EP0006987A1 (de)	1980-01-23	2,4-Diamino-5-benzylpyrimidine, insbesondere zur Behandlung mikrobieller Infektionen, diese Verbindungen enthaltende pharmazeutische Zubereitungen und Verfahren zur Herstellung dieser Verbindungen
JPS5973573A (ja)	1984-04-25	ジアミノピリミジン化合物