CA1129410A - Amidino-benzylpyrimidines, processes for their manufacture and drugs containing the said compounds - Google Patents

Amidino-benzylpyrimidines, processes for their manufacture and drugs containing the said compounds

Info

Publication number: CA1129410A
Authority: CA; Canada
Prior art keywords: pyrimidin; amino; trimethoxybenzyl; acetamidine; process according
Prior art date: 1977-07-15
Legal status (The legal status 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 status listed.): Expired

Application number

CA307,427A

Other languages

English (en)

French (fr)

Inventor

Peter Scharwaechter

Klaus Gutsche

Wilhelm Kohlmann

Gerhard Kroemer (Deceased)

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

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

1982-08-10

1978-07-14 Application filed by BASF SE filed Critical BASF SE

1982-08-10 Application granted granted Critical

1982-08-10 Publication of CA1129410A publication Critical patent/CA1129410A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 55
150000001875 compounds Chemical class 0.000 title claims abstract description 39
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 title claims description 4
229940079593 drug Drugs 0.000 title abstract description 3
239000003814 drug Substances 0.000 title abstract description 3
238000004519 manufacturing process Methods 0.000 title 1
239000002253 acid Substances 0.000 claims abstract description 96
150000003839 salts Chemical class 0.000 claims abstract description 51
150000007513 acids Chemical class 0.000 claims abstract description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
125000004494 ethyl ester group Chemical group 0.000 claims description 45
-1 polymethylene Polymers 0.000 claims description 28
239000002904 solvent Substances 0.000 claims description 27
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
GPTONYMQFTZPKC-UHFFFAOYSA-N sulfamethoxydiazine Chemical compound N1=CC(OC)=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 GPTONYMQFTZPKC-UHFFFAOYSA-N 0.000 claims description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 6
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
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 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
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 claims description 5
PAXRVGDTBDATMF-UHFFFAOYSA-N n,n-dimethylethanimidamide Chemical compound CN(C)C(C)=N PAXRVGDTBDATMF-UHFFFAOYSA-N 0.000 claims description 5
SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 5
QPPBRPIAZZHUNT-UHFFFAOYSA-N sulfamerazine Chemical compound CC1=CC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 QPPBRPIAZZHUNT-UHFFFAOYSA-N 0.000 claims description 5
KXRZBTAEDBELFD-UHFFFAOYSA-N sulfamethopyrazine Chemical compound COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 KXRZBTAEDBELFD-UHFFFAOYSA-N 0.000 claims description 5
VLYWMPOKSSWJAL-UHFFFAOYSA-N sulfamethoxypyridazine Chemical compound N1=NC(OC)=CC=C1NS(=O)(=O)C1=CC=C(N)C=C1 VLYWMPOKSSWJAL-UHFFFAOYSA-N 0.000 claims description 5
GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 claims description 5
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
BRBKOPJOKNSWSG-UHFFFAOYSA-N sulfaguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1 BRBKOPJOKNSWSG-UHFFFAOYSA-N 0.000 claims description 4
229960004257 sulfaguanidine Drugs 0.000 claims description 4
JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 claims description 4
YUPUSBMJCFBHAP-UHFFFAOYSA-N (3,4,5-trimethoxyphenyl)methanamine Chemical compound COC1=CC(CN)=CC(OC)=C1OC YUPUSBMJCFBHAP-UHFFFAOYSA-N 0.000 claims description 3
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
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 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
DVOZVESGYPSPAC-UHFFFAOYSA-N n-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]-n'-[(3,4,5-trimethoxyphenyl)methyl]ethanimidamide Chemical compound COC1=C(OC)C(OC)=CC(CN=C(C)NC=2N=C(N)C(CC=3C=C(OC)C(OC)=C(OC)C=3)=CN=2)=C1 DVOZVESGYPSPAC-UHFFFAOYSA-N 0.000 claims description 3
QKPRBANSEITFLE-UHFFFAOYSA-N n-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]-n'-cyclohexylethanimidamide Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(NC(C)=NC3CCCCC3)=NC=2)N)=C1 QKPRBANSEITFLE-UHFFFAOYSA-N 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 3
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
RIDZDFSSGFEITC-UHFFFAOYSA-N 2-amino-n-(4-propan-2-ylpyrimidin-2-yl)benzenesulfonamide Chemical compound CC(C)C1=CC=NC(NS(=O)(=O)C=2C(=CC=CC=2)N)=N1 RIDZDFSSGFEITC-UHFFFAOYSA-N 0.000 claims description 2
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 claims description 2
229960003805 amantadine Drugs 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
239000000126 substance Substances 0.000 claims 24
125000001701 trimethoxybenzyl group Chemical group 0.000 claims 3
125000005842 heteroatom Chemical group 0.000 claims 2
WXNNXJCMRBGMCX-UHFFFAOYSA-N n-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]-n'-(furan-2-ylmethyl)ethanimidamide Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(NC(C)=NCC=3OC=CC=3)=NC=2)N)=C1 WXNNXJCMRBGMCX-UHFFFAOYSA-N 0.000 claims 2
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
VHEQIKOHDPIQJX-UHFFFAOYSA-N 4-amino-5-benzylpyrimidine-2-carboximidamide Chemical class NC1=NC(C(=N)N)=NC=C1CC1=CC=CC=C1 VHEQIKOHDPIQJX-UHFFFAOYSA-N 0.000 abstract 1
208000035473 Communicable disease Diseases 0.000 abstract 1
238000002844 melting Methods 0.000 description 22
230000008018 melting Effects 0.000 description 22
239000000203 mixture Substances 0.000 description 16
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
239000000243 solution Substances 0.000 description 9
229920002261 Corn starch Polymers 0.000 description 8
108010010803 Gelatin Proteins 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000008120 corn starch Substances 0.000 description 8
229920000159 gelatin Polymers 0.000 description 8
239000008273 gelatin Substances 0.000 description 8
235000019322 gelatine Nutrition 0.000 description 8
235000011852 gelatine desserts Nutrition 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
239000000454 talc Substances 0.000 description 6
229910052623 talc Inorganic materials 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
235000019359 magnesium stearate Nutrition 0.000 description 5
229940124530 sulfonamide Drugs 0.000 description 5
150000003456 sulfonamides Chemical class 0.000 description 5
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 4
239000008187 granular material Substances 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
229920000715 Mucilage Polymers 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
229920003110 Primojel Polymers 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
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
150000001409 amidines Chemical class 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229940127089 cytotoxic agent Drugs 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 2
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
229960003415 propylparaben Drugs 0.000 description 2
239000013558 reference substance Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229940030998 streptococcus agalactiae Drugs 0.000 description 2
229960000468 sulfalene Drugs 0.000 description 2
239000003826 tablet Substances 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
AKUSZFPCJFNRSZ-UHFFFAOYSA-N 3,4-dimethyl-1,2-oxazole Chemical compound CC1=CON=C1C AKUSZFPCJFNRSZ-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
241000894006 Bacteria Species 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
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101100305983 Mus musculus Rom1 gene Proteins 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
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
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
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238000002474 experimental method Methods 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
229910017604 nitric acid Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
210000000056 organ 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
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229960004306 sulfadiazine Drugs 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
235000012222 talc Nutrition 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)

CA307,427A 1977-07-15 1978-07-14 Amidino-benzylpyrimidines, processes for their manufacture and drugs containing the said compounds Expired CA1129410A (en)

Applications Claiming Priority (2)

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
DEP2732029.2		1977-07-15

Publications (1)

Publication Number	Publication Date
CA1129410A true CA1129410A (en)	1982-08-10

Family

ID=6014014

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA307,427A Expired CA1129410A (en)	1977-07-15	1978-07-14	Amidino-benzylpyrimidines, processes for their manufacture and drugs containing the said compounds

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

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4849791A (de) *	1971-10-26	1973-07-13

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

Also Published As

Publication number	Publication date
AT360999B (de)	1981-02-10
AR227759A1 (es)	1982-12-15
EP0000336A1 (de)	1979-01-24
IE47022B1 (en)	1983-11-30
AU520820B2 (en)	1982-03-04
DE2732029A1 (de)	1979-02-01
FI782221A7 (fi)	1979-01-16
DE2860614D1 (en)	1981-05-07
DK315878A (da)	1979-01-16
ATA513078A (de)	1980-07-15
IE781354L (en)	1979-01-15
HU179408B (en)	1982-10-28
DK143273B (da)	1981-08-03
AU3790378A (en)	1980-01-17
EP0000336B1 (de)	1981-04-15
DK143273C (da)	1981-11-30
JPS5419986A (en)	1979-02-15
IT7825382A0 (it)	1978-07-05
IL55063A0 (en)	1978-09-29
ZA784012B (en)	1979-08-29
IT1096976B (it)	1985-08-26
NO782455L (no)	1979-01-16

Legal Events

Date	Code	Title	Description
1999-08-10	MKEX	Expiry

Publication	Publication Date	Title
US4323570A (en)	1982-04-06	Substituted aminopyrimidines
DK172884B1 (da)	1999-09-06	Analogifremgangsmåde til fremstilling af i 5-stilling substituerede 2,4-diaminopyrimidiner og mellemprodukter til anvendels
AU704839B2 (en)	1999-05-06	The use of heterocyclic compounds
AU593640B2 (en)	1990-02-15	Thienopyrimidine-2,4-dione derivatives
JPS6136831B2 (de)	1986-08-20
KR870001027B1 (ko)	1987-05-25	카르복시이미드 유도체의 제조방법
US4792557A (en)	1988-12-20	2,4-diamino-5[4-amino (or dimethylamino)-3,5-dimethoxybenzyl]pyrimidine and antibacterial composition thereof
HU178203B (en)	1982-03-28	Process for producing sulfonamido-pyridine derivatives
EP0029663B1 (de)	1984-04-18	N-Aryl-N'-imidazol-2-yl-harnstoffe, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
CA1314881C (en)	1993-03-23	Anti-anxiety agents
CA1102324A (en)	1981-06-02	Benzylpyrimidines, processes for their manufacture, and drugs containing the said compounds
CA2031147A1 (en)	1991-06-02	Anthelmintics
EP0069784A1 (de)	1983-01-19	Thiazolylharnstoffabkömmlinge, verfahren zu deren herstellung und sie enthaltendes arzneimittel
US4753940A (en)	1988-06-28	Barbituric acid derivatives
US3432493A (en)	1969-03-11	Substituted sulfanilamides
Howard et al.	1953	Piperazines. II. 1-Heterocyclicpiperazines and 1-Hetero-Cyclic-4-Carbethoxypiperazines
IE47022B1 (en)	1983-11-30	Novel amidino-benzylpyrimidines, processes for their manufacture and drugs containing the said compounds
US4189581A (en)	1980-02-19	2-Acylamino-4-amino-5-(3,4,5-trimethoxybenzyl)-pyrimidines
US4128643A (en)	1978-12-05	4-Quinazolinyl-guanidines
US4333936A (en)	1982-06-08	Novel amidino-benzylpyrimidines, processes for their manufacture and antibacterial and antiprotozoal use thereof
ROTH et al.	1961	5-Arylthiopyrimidines. II. 2-and 4-Alkylamino and 4-Amino Derivatives1
CA1107733A (en)	1981-08-25	N-pyrimidinyl-imidoacid esters, processes for their preparation, and drugs containing the said compounds
US3134778A (en)	1964-05-26	2,5,7-triamino-4-phenyl (or thienyl)-pyrimido[4,5-d]pyrimidines
CA1252787A (en)	1989-04-18	Substituted 5-(2-amino-phenylthio)-6-amino- pyrimidinone
KR820001321B1 (ko)	1982-07-23	N-피리미디닐-이미도산 에스테르의 제조방법