NO782455L - Fremgangsmaate for fremstilling av farmakologisk aktive amidino-benzylpyrimidiner - Google Patents

Fremgangsmaate for fremstilling av farmakologisk aktive amidino-benzylpyrimidiner

Info

Publication number: NO782455L
Authority: NO; Norway
Prior art keywords: pyrimidin; trimethoxybenzyl; amino; phenyl; methyl
Prior art date: 1977-07-15

Application number

NO782455A

Other languages

English (en)

Norwegian (no)

Inventor

Peter Scharwaechter

Klaus Gutsche

Wilhelm Kohlmann

Elmshorn Gerhard

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.)

1977-07-15

Filing date

1978-07-14

Publication date

1979-01-16

1978-07-14 Application filed by Basf Ag filed Critical Basf Ag

1979-01-16 Publication of NO782455L publication Critical patent/NO782455L/no

Links

238000002360 preparation method Methods 0.000 title claims description 11
238000000034 method Methods 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 20
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
SEGRUSPUYBBCGO-UHFFFAOYSA-N 2-benzylpyrimidine-4-carboximidamide Chemical class NC(=N)C1=CC=NC(CC=2C=CC=CC=2)=N1 SEGRUSPUYBBCGO-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 1
239000000463 material Substances 0.000 claims 1
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 description 15
-1 alkyl radical Chemical class 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
229940124530 sulfonamide Drugs 0.000 description 6
150000003456 sulfonamides Chemical class 0.000 description 6
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 6
229960001082 trimethoprim Drugs 0.000 description 6
KXRZBTAEDBELFD-UHFFFAOYSA-N sulfamethopyrazine Chemical compound COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 KXRZBTAEDBELFD-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
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 4
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 4
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 4
GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-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
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 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
239000000203 mixture Substances 0.000 description 3
SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 3
BRBKOPJOKNSWSG-UHFFFAOYSA-N sulfaguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1 BRBKOPJOKNSWSG-UHFFFAOYSA-N 0.000 description 3
229960004257 sulfaguanidine Drugs 0.000 description 3
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 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
YUPUSBMJCFBHAP-UHFFFAOYSA-N (3,4,5-trimethoxyphenyl)methanamine Chemical compound COC1=CC(CN)=CC(OC)=C1OC YUPUSBMJCFBHAP-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
FAOKSJPMIMPHQI-UHFFFAOYSA-N 2-amino-n-(5-propan-2-ylpyrimidin-2-yl)benzenesulfonamide Chemical compound N1=CC(C(C)C)=CN=C1NS(=O)(=O)C1=CC=CC=C1N FAOKSJPMIMPHQI-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
241000193985 Streptococcus agalactiae Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001409 amidines Chemical class 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
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 2
150000002463 imidates Chemical class 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000013558 reference substance Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229960000468 sulfalene Drugs 0.000 description 2
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
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-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
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
208000035473 Communicable disease Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
208000005141 Otitis Diseases 0.000 description 1
206010040047 Sepsis Diseases 0.000 description 1
NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 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
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 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
238000001816 cooling Methods 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
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
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
201000004792 malaria Diseases 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
238000002156 mixing Methods 0.000 description 1
UDHCPUCTTVSAIU-UHFFFAOYSA-N n'-(1-adamantyl)-n-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]ethanimidamide Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(NC(C)=NC34CC5CC(CC(C5)C3)C4)=NC=2)N)=C1 UDHCPUCTTVSAIU-UHFFFAOYSA-N 0.000 description 1
PIQTVUVENKVCOE-UHFFFAOYSA-N n'-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]-n-phenylethanimidamide Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(NC(C)=NC=3C=CC=CC=3)=NC=2)N)=C1 PIQTVUVENKVCOE-UHFFFAOYSA-N 0.000 description 1
TXYDGOFEHGQECP-UHFFFAOYSA-N n'-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]ethanimidamide Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(NC(C)=N)=NC=2)N)=C1 TXYDGOFEHGQECP-UHFFFAOYSA-N 0.000 description 1
PAXRVGDTBDATMF-UHFFFAOYSA-N n,n-dimethylethanimidamide Chemical compound CN(C)C(C)=N PAXRVGDTBDATMF-UHFFFAOYSA-N 0.000 description 1
MPXXIGSUCCSTEZ-UHFFFAOYSA-N n-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]-n'-benzylethanimidamide Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(NC(C)=NCC=3C=CC=CC=3)=NC=2)N)=C1 MPXXIGSUCCSTEZ-UHFFFAOYSA-N 0.000 description 1
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
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229960004306 sulfadiazine Drugs 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
229960002597 sulfamerazine Drugs 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
229960005404 sulfamethoxazole Drugs 0.000 description 1
229960004936 sulfamethoxypyridazine Drugs 0.000 description 1
229960002229 sulfametoxydiazine Drugs 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
229960000277 sulfaperin Drugs 0.000 description 1
DZQVFHSCSRACSX-UHFFFAOYSA-N sulfaperin Chemical compound N1=CC(C)=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 DZQVFHSCSRACSX-UHFFFAOYSA-N 0.000 description 1
229960002211 sulfapyridine Drugs 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
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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO782455A 1977-07-15 1978-07-14 Fremgangsmaate for fremstilling av farmakologisk aktive amidino-benzylpyrimidiner NO782455L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772732029 DE2732029A1 (de)	1977-07-15	1977-07-15	Neue amidino-benzylpyrimidine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
NO782455L true NO782455L (no)	1979-01-16

Family

ID=6014014

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO782455A NO782455L (no)	1977-07-15	1978-07-14	Fremgangsmaate for fremstilling av farmakologisk aktive amidino-benzylpyrimidiner

Country Status (15)

Country	Link
EP (1)	EP0000336B1 (de)
JP (1)	JPS5419986A (de)
AR (1)	AR227759A1 (de)
AT (1)	AT360999B (de)
AU (1)	AU520820B2 (de)
CA (1)	CA1129410A (de)
DE (2)	DE2732029A1 (de)
DK (1)	DK143273C (de)
FI (1)	FI782221A7 (de)
HU (1)	HU179408B (de)
IE (1)	IE47022B1 (de)
IL (1)	IL55063A0 (de)
IT (1)	IT1096976B (de)
NO (1)	NO782455L (de)
ZA (1)	ZA784012B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2730468A1 (de) *	1977-07-06	1979-01-18	Basf Ag	Neue n-pyrimidinyl-imidsaeureester, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
US4333936A (en) *	1978-07-03	1982-06-08	Basf Aktiengesellschaft	Novel amidino-benzylpyrimidines, processes for their manufacture and antibacterial and antiprotozoal use thereof
DE3045720A1 (de) *	1980-12-04	1982-07-08	Basf Ag, 6700 Ludwigshafen	N-pyrimidinyl-carbaminsaeureester, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
JPS5915110U (ja) *	1982-07-22	1984-01-30	クラリオン株式会社	定電圧回路
JPH0618012B2 (ja) *	1983-01-25	1994-03-09	セイコーエプソン株式会社	定電圧回路

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JPS4849791A (de) *	1971-10-26	1973-07-13

1977
- 1977-07-15 DE DE19772732029 patent/DE2732029A1/de not_active Withdrawn
1978
- 1978-06-19 EP EP78100184A patent/EP0000336B1/de not_active Expired
- 1978-06-19 DE DE7878100184T patent/DE2860614D1/de not_active Expired
- 1978-07-03 IL IL55063A patent/IL55063A0/xx unknown
- 1978-07-05 IT IT25382/78A patent/IT1096976B/it active
- 1978-07-05 IE IE1354/78A patent/IE47022B1/en unknown
- 1978-07-10 AU AU37903/78A patent/AU520820B2/en not_active Expired
- 1978-07-11 FI FI782221A patent/FI782221A7/fi not_active Application Discontinuation
- 1978-07-11 AR AR272912A patent/AR227759A1/es active
- 1978-07-13 HU HU78BA3676A patent/HU179408B/hu unknown
- 1978-07-13 JP JP8462878A patent/JPS5419986A/ja active Pending
- 1978-07-14 NO NO782455A patent/NO782455L/no unknown
- 1978-07-14 AT AT513078A patent/AT360999B/de not_active IP Right Cessation
- 1978-07-14 CA CA307,427A patent/CA1129410A/en not_active Expired
- 1978-07-14 ZA ZA00784012A patent/ZA784012B/xx unknown
- 1978-07-14 DK DK315878A patent/DK143273C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0000336A1 (de)	1979-01-24
IT7825382A0 (it)	1978-07-05
AU520820B2 (en)	1982-03-04
ZA784012B (en)	1979-08-29
AT360999B (de)	1981-02-10
IL55063A0 (en)	1978-09-29
DK143273C (da)	1981-11-30
CA1129410A (en)	1982-08-10
JPS5419986A (en)	1979-02-15
DK143273B (da)	1981-08-03
DE2860614D1 (en)	1981-05-07
FI782221A7 (fi)	1979-01-16
HU179408B (en)	1982-10-28
IT1096976B (it)	1985-08-26
EP0000336B1 (de)	1981-04-15
ATA513078A (de)	1980-07-15
IE47022B1 (en)	1983-11-30
IE781354L (en)	1979-01-15
AR227759A1 (es)	1982-12-15
AU3790378A (en)	1980-01-17
DK315878A (da)	1979-01-16
DE2732029A1 (de)	1979-02-01

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