NO813258L - Nye 2-aminoimidazoler, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse, samt deres anvendelse - Google Patents

Nye 2-aminoimidazoler, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse, samt deres anvendelse

Info

Publication number: NO813258L
Authority: NO; Norway
Prior art keywords: imidazolo; produced; rifamycin; formula; piperazinyl
Prior art date: 1980-09-25

Application number

NO813258A

Other languages

English (en)

Norwegian (no)

Inventor

Wilhelm Kump

Peter Traxler

Riccardo Scartazzini

Original Assignee

Ciba Geigy 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.)

1980-09-25

Filing date

1981-09-24

Publication date

1982-03-26

1981-09-24 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1982-03-26 Publication of NO813258L publication Critical patent/NO813258L/no

Links

238000000034 method Methods 0.000 title claims description 135
238000002360 preparation method Methods 0.000 title claims description 14
239000000825 pharmaceutical preparation Substances 0.000 title claims description 12
-1 3-aminorifamycin-S compound Chemical class 0.000 claims description 190
150000001875 compounds Chemical class 0.000 claims description 130
229940109171 rifamycin sv Drugs 0.000 claims description 72
HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical compound OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 claims description 63
150000003839 salts Chemical class 0.000 claims description 52
125000000217 alkyl group Chemical group 0.000 claims description 41
HJYYPODYNSCCOU-ZDHWWVNNSA-N Rifamycin SV Natural products COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C)cc(O)c4c3C2=O HJYYPODYNSCCOU-ZDHWWVNNSA-N 0.000 claims description 37
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 34
238000006243 chemical reaction Methods 0.000 claims description 30
239000013543 active substance Substances 0.000 claims description 28
229910052757 nitrogen Inorganic materials 0.000 claims description 24
125000000623 heterocyclic group Chemical group 0.000 claims description 23
125000001183 hydrocarbyl group Chemical group 0.000 claims description 21
125000003277 amino group Chemical group 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 19
239000000126 substance Substances 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
239000001301 oxygen Substances 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 13
229960003292 rifamycin Drugs 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 claims description 10
229930195573 Amycin Natural products 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
229910021529 ammonia Inorganic materials 0.000 claims description 9
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
239000005864 Sulphur Substances 0.000 claims description 7
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims description 7
125000002950 monocyclic group Chemical group 0.000 claims description 7
230000002829 reductive effect Effects 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229930189077 Rifamycin Natural products 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
125000004043 oxo group Chemical group O=* 0.000 claims description 5
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
150000002829 nitrogen Chemical class 0.000 claims description 4
230000036961 partial effect Effects 0.000 claims description 4
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
125000002619 bicyclic group Chemical group 0.000 claims description 3
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 3
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
208000015181 infectious disease Diseases 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 3
HUMIEJNVCICTPJ-UHFFFAOYSA-N 2,2-dimethoxy-n-methylethanamine Chemical compound CNCC(OC)OC HUMIEJNVCICTPJ-UHFFFAOYSA-N 0.000 claims description 2
125000006077 2-ethyl-2-butenyl group Chemical group 0.000 claims description 2
125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims description 2
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
125000004151 quinonyl group Chemical group 0.000 claims description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
230000000813 microbial effect Effects 0.000 claims 2
229960005041 troleandomycin Drugs 0.000 claims 2
125000005917 3-methylpentyl group Chemical group 0.000 claims 1
QRZMXADUXZADTF-UHFFFAOYSA-N 4-aminoimidazole Chemical compound NC1=CNC=N1 QRZMXADUXZADTF-UHFFFAOYSA-N 0.000 claims 1
241000009298 Trigla lyra Species 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 claims 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 195
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
239000003153 chemical reaction reagent Substances 0.000 description 89
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 70
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 66
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
239000000243 solution Substances 0.000 description 58
QBRFPWPICDILII-WVKYYCEASA-N 3-amino-4-iminorifamycin-s Chemical compound O=C1C(C(O)=C2C)=C3C(N)=C(N)C1=NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O QBRFPWPICDILII-WVKYYCEASA-N 0.000 description 55
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
235000002639 sodium chloride Nutrition 0.000 description 46
239000000203 mixture Substances 0.000 description 39
239000002253 acid Substances 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
239000000843 powder Substances 0.000 description 22
239000000741 silica gel Substances 0.000 description 22
229910002027 silica gel Inorganic materials 0.000 description 22
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
SMPJCQGFZSDIHE-GVDHMVJUSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-amino-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate Chemical compound O=C1C(C(O)=C2C)=C3C(=O)C(N)=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O SMPJCQGFZSDIHE-GVDHMVJUSA-N 0.000 description 17
239000000047 product Substances 0.000 description 17
125000001424 substituent group Chemical group 0.000 description 17
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 15
238000002425 crystallisation Methods 0.000 description 15
230000008025 crystallization Effects 0.000 description 15
238000009835 boiling Methods 0.000 description 14
238000010828 elution Methods 0.000 description 13
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 12
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
238000010992 reflux Methods 0.000 description 11
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
238000000354 decomposition reaction Methods 0.000 description 10
238000001704 evaporation Methods 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
150000001241 acetals Chemical class 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 9
239000000284 extract Substances 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
125000002015 acyclic group Chemical group 0.000 description 7
239000002585 base Substances 0.000 description 7
125000002837 carbocyclic group Chemical group 0.000 description 7
239000000376 reactant Substances 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
150000003335 secondary amines Chemical class 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
239000002775 capsule Substances 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
239000003480 eluent Substances 0.000 description 6
150000003948 formamides Chemical class 0.000 description 6
238000004508 fractional distillation Methods 0.000 description 6
239000007788 liquid Substances 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
BTVYFIMKUHNOBZ-ZDHWWVNNSA-N Rifamycin S Natural products COC1C=COC2(C)Oc3c(C)c(O)c4C(=O)C(=CC(=O)c4c3C2=O)NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C BTVYFIMKUHNOBZ-ZDHWWVNNSA-N 0.000 description 5
229920005654 Sephadex Polymers 0.000 description 5
239000012507 Sephadex™ Substances 0.000 description 5
229920002472 Starch Polymers 0.000 description 5
150000001793 charged compounds Chemical class 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
238000003776 cleavage reaction Methods 0.000 description 5
ZYMLBOINJTXUAK-UHFFFAOYSA-N dimethoxymethanamine Chemical compound COC(N)OC ZYMLBOINJTXUAK-UHFFFAOYSA-N 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
230000007017 scission Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
239000007858 starting material Substances 0.000 description 5
230000007306 turnover Effects 0.000 description 5
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 4
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
BTVYFIMKUHNOBZ-ODRIEIDWSA-N Rifamycin S Chemical compound O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-ODRIEIDWSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
150000001408 amides Chemical group 0.000 description 4
150000003863 ammonium salts Chemical class 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000001819 mass spectrum Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 4
244000005700 microbiome Species 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
125000004193 piperazinyl group Chemical group 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000005916 2-methylpentyl group Chemical group 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
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 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241000191967 Staphylococcus aureus Species 0.000 description 3
235000021355 Stearic acid Nutrition 0.000 description 3
125000004442 acylamino group Chemical group 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
230000000845 anti-microbial effect Effects 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
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UBLYEVLMRSPMOG-UHFFFAOYSA-N cyclopentylmethanamine Chemical compound NCC1CCCC1 UBLYEVLMRSPMOG-UHFFFAOYSA-N 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 description 1
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239000003085 diluting agent Substances 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
231100000676 disease causative agent Toxicity 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
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238000000921 elemental analysis Methods 0.000 description 1
230000008029 eradication Effects 0.000 description 1
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230000002349 favourable effect Effects 0.000 description 1
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239000011630 iodine Substances 0.000 description 1
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125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
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WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 description 1
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229960003424 phenylacetic acid Drugs 0.000 description 1
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125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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239000011591 potassium Substances 0.000 description 1
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TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
229940005657 pyrophosphoric acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000009666 routine test Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
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239000005720 sucrose Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000001730 thiiranyl group Chemical group 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical class OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
WAXSLAPFZTWPTR-UHFFFAOYSA-N trimethyl-(2-methyl-1-piperazin-1-ylpropan-2-yl)oxysilane Chemical compound C[Si](C)(C)OC(C)(C)CN1CCNCC1 WAXSLAPFZTWPTR-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1
239000004474 valine Substances 0.000 description 1
239000002966 varnish Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO813258A 1980-09-25 1981-09-24 Nye 2-aminoimidazoler, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse, samt deres anvendelse NO813258L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH718580		1980-09-25
CH718480		1980-09-25

Publications (1)

Publication Number	Publication Date
NO813258L true NO813258L (no)	1982-03-26

Family

ID=25700906

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO813258A NO813258L (no)	1980-09-25	1981-09-24	Nye 2-aminoimidazoler, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse, samt deres anvendelse

Country Status (13)

Country	Link
EP (1)	EP0049683A3 (fi)
KR (1)	KR830007667A (fi)
AU (1)	AU7559481A (fi)
DD (1)	DD204925A5 (fi)
DK (1)	DK421981A (fi)
ES (2)	ES505723A0 (fi)
FI (1)	FI812936L (fi)
GB (1)	GB2084575A (fi)
GR (1)	GR75352B (fi)
IL (1)	IL63917A0 (fi)
NO (1)	NO813258L (fi)
PL (1)	PL233180A1 (fi)
PT (1)	PT73726B (fi)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5099019A (en) *	1985-09-12	1992-03-24	Upjohn Company	Amines useful in producing pharmaceutically active CNS compounds
USRE35053E (en) *	1985-09-12	1995-10-10	The Upjohn Company	Amines useful in producing pharmaceutically active CNS compounds
US5382661A (en) *	1985-09-12	1995-01-17	The Upjohn Company	Pyrazinylpiperazinyl steroids
GB8531887D0 (en) *	1985-12-30	1986-02-05	Lepetit Spa	Rifamycin sv derivatives
IT1253711B (it) *	1991-12-17	1995-08-23	Alfa Wassermann Spa	Formulazioni farmaceutiche vaginali contenenti rifaximin e loro uso nel trattamento delle infezioni vaginali

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GB1172155A (en) *	1967-03-01	1969-11-26	Lepetit Spa	New Rifamycins
DK345977A (da) *	1976-09-30	1978-03-31	Archifar Ind Chim Trentino	G rifamycinforbindelser og fremgangsmaade til deres fremstillin
GB2069485B (en) *	1980-02-13	1983-11-23	Erba Farmitalia	Rifamycin derivatives

1981
- 1981-09-21 FI FI812936A patent/FI812936L/fi not_active Application Discontinuation
- 1981-09-21 EP EP81810387A patent/EP0049683A3/de not_active Withdrawn
- 1981-09-21 DD DD81247258A patent/DD204925A5/de unknown
- 1981-09-23 GR GR66112A patent/GR75352B/el unknown
- 1981-09-23 GB GB8128704A patent/GB2084575A/en not_active Withdrawn
- 1981-09-23 AU AU75594/81A patent/AU7559481A/en not_active Abandoned
- 1981-09-23 ES ES505723A patent/ES505723A0/es active Granted
- 1981-09-23 IL IL63917A patent/IL63917A0/xx unknown
- 1981-09-24 PT PT73726A patent/PT73726B/pt unknown
- 1981-09-24 PL PL23318081A patent/PL233180A1/xx unknown
- 1981-09-24 DK DK421981A patent/DK421981A/da unknown
- 1981-09-24 NO NO813258A patent/NO813258L/no unknown
- 1981-09-25 KR KR1019810003593A patent/KR830007667A/ko unknown
1982
- 1982-08-10 ES ES514883A patent/ES514883A0/es active Granted

Also Published As

Publication number	Publication date
ES8306487A1 (es)	1983-06-01
EP0049683A3 (de)	1982-09-01
ES8302732A1 (es)	1982-12-01
PT73726B (de)	1983-10-19
PT73726A (de)	1981-10-01
ES505723A0 (es)	1982-12-01
GB2084575A (en)	1982-04-15
PL233180A1 (en)	1983-02-14
KR830007667A (ko)	1983-11-04
DK421981A (da)	1982-03-26
DD204925A5 (de)	1983-12-14
FI812936L (fi)	1982-03-26
IL63917A0 (en)	1981-12-31
EP0049683A2 (de)	1982-04-14
ES514883A0 (es)	1983-06-01
GR75352B (fi)	1984-07-13
AU7559481A (en)	1982-04-01

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