LV10951B - 4-quinolinyl derivatives with anti-helicobacter activity - Google Patents
4-quinolinyl derivatives with anti-helicobacter activity Download PDFInfo
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- LV10951B LV10951B LVP-95-143A LV950143A LV10951B LV 10951 B LV10951 B LV 10951B LV 950143 A LV950143 A LV 950143A LV 10951 B LV10951 B LV 10951B
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- acid
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- 230000000694 effects Effects 0.000 title abstract description 13
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical class [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 115
- 239000000203 mixture Substances 0.000 claims abstract description 82
- 239000002253 acid Substances 0.000 claims abstract description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 4
- -1 nitro, amino Chemical group 0.000 claims description 35
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 239000012442 inert solvent Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
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- 239000004480 active ingredient Substances 0.000 claims description 7
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- 150000001622 bismuth compounds Chemical class 0.000 claims description 6
- 229940126409 proton pump inhibitor Drugs 0.000 claims description 5
- 239000000612 proton pump inhibitor Substances 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 230000009466 transformation Effects 0.000 claims description 4
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- BBRATVCTCKUNNY-UHFFFAOYSA-N 4-[(3-chlorophenyl)-(1,2,4-triazol-1-yl)methyl]quinoline Chemical class ClC1=CC=CC(C(C=2C3=CC=CC=C3N=CC=2)N2N=CN=C2)=C1 BBRATVCTCKUNNY-UHFFFAOYSA-N 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 7
- 208000035475 disorder Diseases 0.000 abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 abstract description 3
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 abstract description 3
- 206010019375 Helicobacter infections Diseases 0.000 abstract description 2
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 53
- 239000000543 intermediate Substances 0.000 description 46
- 125000001309 chloro group Chemical group Cl* 0.000 description 38
- 239000000243 solution Substances 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 125000005843 halogen group Chemical group 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 20
- 241000206607 Porphyra umbilicalis Species 0.000 description 19
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 15
- 239000003480 eluent Substances 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 12
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- 229910002027 silica gel Inorganic materials 0.000 description 12
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 11
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 125000001246 bromo group Chemical group Br* 0.000 description 8
- 241000589989 Helicobacter Species 0.000 description 6
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 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 5
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- 125000001153 fluoro group Chemical group F* 0.000 description 5
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- SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical compound N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 description 1
- 229960000381 omeprazole Drugs 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 229940098462 oral drops Drugs 0.000 description 1
- 150000002891 organic anions Chemical group 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical class C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000004508 retinoic acid derivatives Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000004114 suspension culture Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Claims (4)
- LV 10951 PATENTA FORMULA 1. Savienojums ar formulu r'tā farmaceitiski saderīgs pievienotas skābes sāls, tā stereoķīmiska izomēra forma, tā kvaternizēta forma vai tā Ņ-oksids, kur -A- apzīmē divvērtīgu radikālu ar formulu -N=CH-CH=CH- (a), -CH=N-CH=CH- (b), -N=N-CH=CH- (c), -N=CH-N=CH- (d), -N=CH-CH=N- (e), -CH=N-N=CH- (f). -N=N-N=CH- (g). -N=N-CH=N- (h) vai -CH=CH-CH=CH- CO; R1, R1, R3, R4, R5, R6 un R7 katrs neatkarīgi apzīmē ūdeņradi, halogēnu, hidroksilgrupu, C,.4alkiloksigrupu, C,.4alkilgrupu, trifluor-metilgrupu, aminogrupu, mono- vai di-(C,.4alkil)aminogrupu vai nitrogrupu, nodrošinot, ka, ja viens aizvietotājs fenilgrupā ir nitrogrupa, tad otrs aizvietotājs minētajā fenilgrupā ir citāds, kā nitrogrupa. 1 Savienojums, saskaņā ar 1. punktu, kur
- 2 R' apzīmē ūdeņradi, C,.4alkilgrupu, hidroksilgrupu, C^alkil-oksigrupu, nitrogrupu, aminogrupu vai mono* vai di-(C,.4al-kil)aminogrupu; R2, R3 un R4 katrs neatkarīgi apzīmē ūdeņradi, halogēnu, trifluor-metilgrupu, hidroksilgrupu vai C,.4alkiloksigrupu; R5 apzīmē ūdeņradi, halogēnu, hidroksilgrupu vai C^alkil-oksigrupu; R6 un R1 katrs neatkarīgi apzīmē ūdeņradi, halogēnu, hidroksilgrupu, C,.4alkiloksigrupu vai trifluormetilgrupu.
- 3. Savienojums, saskaņā ar 2. punktu, kur R', R2, R3, R5 un R6 apzīmē ūdeņradi, un R4 un R1 katrs neatkarīgi apzīmē ūdeņradi vai halogēnu.4. Savienojums, saskaņā ar 3. punktu, kur -A- apzīmē divvērtīgu radikālu ar formulu -N=N-CH=CH- (c) vai -N=CH-N=CH- (d) un R4 ir 3-halogēns.5. Savienojums, saskaņā ar 4, punktu, kas ir izvēlēts no grupas, kas sastāv no 4-[(3-hlorfenil)(1H-1,2,4-triazol-1-il)metil]hinolīna, tā farmaceitiski saderīgiem pievienotas skābes sāļiem, tā stereoķīmisko izomēru formām, tā kvaternizētām formām un tā Ņ-oksidiem.6. Farmaceitisks sastāvs, kas kā aktīvo sastāvdaļu satur savienojuma, saskaņā ar jebkuru no 1. līdz 5. punktiem, terapeitiski efektīvu daudzumu un farmaceitiski saderīgu nesēju. 1 Farmaceitisks sastāvs, saskaņā ar 6. punktu, atšķirīgs ar to, ka tas bez tam satur terapeitiski efektīvu daudzumu protonu sūkņa inhibitora vai terapeitiski efektīvu daudzumu bismuta savienojuma, vai terapeitiski efektīvu daudzumu protonu sūkņa inhibitora un bismuta savienojuma kombinācijas. 3 LV 109518. Metode sastāva, saskaņā ar 6. punktu, iegūšanai, atšķirīga ar to, ka aktīvā ingredienta terapeitiski efektīvu daudzumu rūpīgi samaisa ar farmaceitiski saderīgu nesēju.9. Savienojums, saskaņā ar 1. punktu, ko izmanto, kā medikamentu.10. Metode savienojuma, saskaņā ar jebkuru no 1. līdz 5. punktiem, iegūšanai, atšķirīga ar to, ka a) Ņ-alkilē azolu ar formulu (II) ar starpproduktu ar formulu (III) reakcijas apstākļos inertā šķīdinātājā,kur A un R1 - R7 ir, kā norādīts 1. punktā, un W ir reaģējoša atšķeļama grupa, b) liek reaģēt azolam ar formulu (II) ar starpproduktu ar formulu (IV) reakcijas apstākļos inertā šķīdinātājā un reaģenta klātbūtnē, kas transformē hidroksilgrupu starpproduktā (IV) vieglāk atšķeļamā grupā,
- 4 c) liek reaģēt starpproduktam ar formulu (V) ar reaģentu ar formulu (VI), kurā W' ir reaģējoša atšķeļama grupa, tā iegūstot savienojumu ar formulu (l-b), 4d) liek reaģēt starpproduktam ar formulu (VII) ar metānimidamidu vai tā atvasinājumu reakcijas apstākļos inertā šķīdinātājā, tā iegūstot savienojumu ar formulu (l-c), onh=ch-nh2 N-NHun, ja nepieciešams, pārvērš savienojumus ar formulu (I) vienu otrai sekojošās praksē pazīstamās funkcionālo grupu transformēšanas reakcijās un, ja nepieciešams, pārvērš savienojumus ar formulu (I) terapeitiski aktīvā netoksiskā pievienotas skābes sālī, apstrādājot ar skābi, vai pretēji, pārvērš sāls formu brīvā bāzē, apstrādājot ar sārmu; un/vai gatavo to stereoķīmisko izomēru formas; un/vai gatavo to kvaternizētas formas; un/vai gatavo to Ņ-oksīdus.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96700892A | 1992-10-27 | 1992-10-27 | |
| US6980493A | 1993-06-01 | 1993-06-01 | |
| PCT/EP1993/002884 WO1994010164A1 (en) | 1992-10-27 | 1993-10-19 | 4-quinolinyl derivatives with anti-helicobacter activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LV10951A LV10951A (lv) | 1995-12-20 |
| LV10951B true LV10951B (en) | 1996-08-20 |
Family
ID=26750446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-95-143A LV10951B (en) | 1992-10-27 | 1995-05-26 | 4-quinolinyl derivatives with anti-helicobacter activity |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5589484A (lv) |
| EP (1) | EP0666855B1 (lv) |
| JP (1) | JPH08502503A (lv) |
| KR (1) | KR100239003B1 (lv) |
| AT (1) | ATE143013T1 (lv) |
| AU (1) | AU675087B2 (lv) |
| BG (1) | BG99566A (lv) |
| CA (1) | CA2146651A1 (lv) |
| CZ (1) | CZ287159B6 (lv) |
| DE (1) | DE69304930T2 (lv) |
| DK (1) | DK0666855T3 (lv) |
| ES (1) | ES2094567T3 (lv) |
| FI (1) | FI951996A0 (lv) |
| GR (1) | GR3021690T3 (lv) |
| HU (1) | HUT71895A (lv) |
| LV (1) | LV10951B (lv) |
| NO (1) | NO951588L (lv) |
| NZ (1) | NZ256871A (lv) |
| PL (1) | PL175679B1 (lv) |
| RU (1) | RU2130933C1 (lv) |
| SK (1) | SK53495A3 (lv) |
| WO (1) | WO1994010164A1 (lv) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002516323A (ja) | 1998-05-23 | 2002-06-04 | ビイク グルデン ロンベルク ヒエーミツシエ フアブリーク ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | 抗ヘリコバクター活性を有するキノリン−アミノメチル−ピリジル誘導体 |
| GB9819382D0 (en) | 1998-09-04 | 1998-10-28 | Cerebrus Ltd | Chemical compounds I |
| TW200803855A (en) * | 2006-02-24 | 2008-01-16 | Kalypsys Inc | Quinolones useful as inducible nitric oxide synthase inhibitors |
| WO2011082245A2 (en) | 2009-12-31 | 2011-07-07 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| US9302992B2 (en) | 2013-04-02 | 2016-04-05 | Annji Pharmaceutical Co., Ltd. | Multifunctional quinoline derivatives as anti-neurodegenerative agents |
| KR101802048B1 (ko) * | 2013-04-02 | 2017-12-28 | 안지 파마슈티컬 코퍼레이션 리미티드 | 항신경퇴행성제로서의 다작용성 퀴놀린 유도체 |
| JP6254239B2 (ja) * | 2016-02-29 | 2017-12-27 | 大日精化工業株式会社 | ポリマーの製造方法 |
| JP6245719B1 (ja) | 2017-03-24 | 2017-12-13 | 大日精化工業株式会社 | ポリマーの製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT294090B (de) * | 1969-04-22 | 1971-11-10 | Degussa | Verfahren zur Herstellung von neuen Aminopyridinen, von deren optisch aktiven bzw. diastereomeren Formen, deren Salzen und deren quartären Verbindungen |
| CH679582A5 (lv) * | 1988-07-18 | 1992-03-13 | Glaxo Group Ltd | |
| US5185346A (en) * | 1988-11-29 | 1993-02-09 | Hanssen Pharmaceutica | (1H-azol-1-ylmethyl)substituted quinoline derivatives |
| CA2002864C (en) * | 1988-11-29 | 1999-11-16 | Eddy J. E. Freyne | (1h-azol-1-ylmethyl) substituted quinoline, quinazoline or quinoxaline derivatives |
| GB8827820D0 (en) * | 1988-11-29 | 1988-12-29 | Janssen Pharmaceutica Nv | (1h-azol-1-ylmethyl)substituted quinoline derivatives |
| GB8827822D0 (en) * | 1988-11-29 | 1988-12-29 | Janssen Pharmaceutica Nv | (1h-azol-1-ylmethyl)substituted quinoline derivatives |
| US5128140A (en) * | 1991-01-14 | 1992-07-07 | The Procter & Gamble Company | Swallowable pharmaceutical compositions |
-
1993
- 1993-10-19 EP EP93922961A patent/EP0666855B1/en not_active Expired - Lifetime
- 1993-10-19 US US08/428,176 patent/US5589484A/en not_active Expired - Fee Related
- 1993-10-19 SK SK534-95A patent/SK53495A3/sk unknown
- 1993-10-19 DK DK93922961.3T patent/DK0666855T3/da active
- 1993-10-19 JP JP6510636A patent/JPH08502503A/ja active Pending
- 1993-10-19 ES ES93922961T patent/ES2094567T3/es not_active Expired - Lifetime
- 1993-10-19 KR KR1019950701501A patent/KR100239003B1/ko not_active Expired - Fee Related
- 1993-10-19 PL PL93308550A patent/PL175679B1/pl unknown
- 1993-10-19 AT AT93922961T patent/ATE143013T1/de not_active IP Right Cessation
- 1993-10-19 DE DE69304930T patent/DE69304930T2/de not_active Expired - Fee Related
- 1993-10-19 HU HU9501207A patent/HUT71895A/hu unknown
- 1993-10-19 AU AU51782/93A patent/AU675087B2/en not_active Ceased
- 1993-10-19 CA CA002146651A patent/CA2146651A1/en not_active Abandoned
- 1993-10-19 WO PCT/EP1993/002884 patent/WO1994010164A1/en not_active Ceased
- 1993-10-19 CZ CZ1995837A patent/CZ287159B6/cs not_active IP Right Cessation
- 1993-10-19 RU RU95109440A patent/RU2130933C1/ru active
- 1993-10-19 NZ NZ256871A patent/NZ256871A/en unknown
-
1995
- 1995-04-12 BG BG99566A patent/BG99566A/xx unknown
- 1995-04-26 FI FI951996A patent/FI951996A0/fi unknown
- 1995-04-26 NO NO951588A patent/NO951588L/no unknown
- 1995-05-26 LV LVP-95-143A patent/LV10951B/en unknown
-
1996
- 1996-11-18 GR GR960403075T patent/GR3021690T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2094567T3 (es) | 1997-01-16 |
| GR3021690T3 (en) | 1997-02-28 |
| KR950704297A (ko) | 1995-11-17 |
| US5589484A (en) | 1996-12-31 |
| NZ256871A (en) | 1995-09-26 |
| BG99566A (en) | 1996-01-31 |
| HUT71895A (en) | 1996-02-28 |
| EP0666855B1 (en) | 1996-09-18 |
| FI951996A7 (fi) | 1995-04-26 |
| CZ83795A3 (en) | 1995-09-13 |
| ATE143013T1 (de) | 1996-10-15 |
| PL308550A1 (en) | 1995-08-21 |
| LV10951A (lv) | 1995-12-20 |
| EP0666855A1 (en) | 1995-08-16 |
| FI951996A0 (fi) | 1995-04-26 |
| SK53495A3 (en) | 1995-09-13 |
| HU9501207D0 (en) | 1995-06-28 |
| CA2146651A1 (en) | 1994-05-11 |
| NO951588L (no) | 1995-06-27 |
| WO1994010164A1 (en) | 1994-05-11 |
| AU675087B2 (en) | 1997-01-23 |
| JPH08502503A (ja) | 1996-03-19 |
| DE69304930D1 (de) | 1996-10-24 |
| PL175679B1 (pl) | 1999-01-29 |
| AU5178293A (en) | 1994-05-24 |
| CZ287159B6 (en) | 2000-10-11 |
| RU2130933C1 (ru) | 1999-05-27 |
| KR100239003B1 (ko) | 2000-02-01 |
| NO951588D0 (no) | 1995-04-26 |
| RU95109440A (ru) | 1997-03-10 |
| DK0666855T3 (da) | 1996-10-07 |
| DE69304930T2 (de) | 1997-02-27 |
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