CS238624B2 - Production method of chinoline derivatives - Google Patents
Production method of chinoline derivatives Download PDFInfo
- Publication number
- CS238624B2 CS238624B2 CS824253A CS425382A CS238624B2 CS 238624 B2 CS238624 B2 CS 238624B2 CS 824253 A CS824253 A CS 824253A CS 425382 A CS425382 A CS 425382A CS 238624 B2 CS238624 B2 CS 238624B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- compounds
- radical
- acid addition
- formula
- stands
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 15
- -1 heteroaryl radical Chemical class 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 4
- 239000002253 acid Substances 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 5
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003248 quinolines Chemical class 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- HYOLQGVNMQNERE-UHFFFAOYSA-N n,n-dimethyl-2-(3-phenylquinolin-2-yl)sulfanylethanamine Chemical compound CN(C)CCSC1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 HYOLQGVNMQNERE-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract description 6
- 239000003420 antiserotonin agent Substances 0.000 abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 230000027455 binding Effects 0.000 description 5
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 4
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 4
- 229940000681 5-hydroxytryptophan Drugs 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229960001582 fenfluramine Drugs 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000004886 head movement Effects 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 238000000099 in vitro assay Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000009870 specific binding Effects 0.000 description 2
- 229950001675 spiperone Drugs 0.000 description 2
- ZUGSZYLRCNAKOS-UHFFFAOYSA-N 2-[3-(2-methoxyphenyl)quinolin-2-yl]sulfanyl-n,n-dimethylethanamine Chemical compound COC1=CC=CC=C1C1=CC2=CC=CC=C2N=C1SCCN(C)C ZUGSZYLRCNAKOS-UHFFFAOYSA-N 0.000 description 1
- RBWDAFWJSCEAQV-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)quinolin-2-yl]sulfanyl-n,n-dimethylethanamine Chemical compound CN(C)CCSC1=NC2=CC=CC=C2C=C1C1=CC=C(F)C=C1 RBWDAFWJSCEAQV-UHFFFAOYSA-N 0.000 description 1
- LFARBJHRSSLIGX-UHFFFAOYSA-N 2-chloro-3-phenylquinoline Chemical compound ClC1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 LFARBJHRSSLIGX-UHFFFAOYSA-N 0.000 description 1
- 150000005642 2-chloroquinolines Chemical class 0.000 description 1
- 102000035038 5-HT1 receptors Human genes 0.000 description 1
- 108091005478 5-HT1 receptors Proteins 0.000 description 1
- 102000056834 5-HT2 Serotonin Receptors Human genes 0.000 description 1
- 108091005479 5-HT2 receptors Proteins 0.000 description 1
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010020843 Hyperthermia Diseases 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 206010047163 Vasospasm Diseases 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036031 hyperthermia Effects 0.000 description 1
- 230000002977 hyperthermial effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- ARPRLCXPAGXBRL-UHFFFAOYSA-N n,n,2-trimethyl-1-(3-phenylquinolin-2-yl)sulfanylpropan-2-amine Chemical compound CN(C)C(C)(C)CSC1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 ARPRLCXPAGXBRL-UHFFFAOYSA-N 0.000 description 1
- WMSMYWZAPQVNTQ-UHFFFAOYSA-N n,n-diethyl-2-(3-phenylquinolin-2-yl)oxyethanamine Chemical compound CCN(CC)CCOC1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 WMSMYWZAPQVNTQ-UHFFFAOYSA-N 0.000 description 1
- KBSPNHZTNNSAPF-UHFFFAOYSA-N n,n-dimethyl-1-(3-phenylquinolin-2-yl)sulfanylpropan-2-amine Chemical compound CN(C)C(C)CSC1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 KBSPNHZTNNSAPF-UHFFFAOYSA-N 0.000 description 1
- XMRXKCIELMKQPF-UHFFFAOYSA-N n,n-dimethyl-2-(3-phenylquinolin-2-yl)sulfanylethanamine;hydron;chloride Chemical compound Cl.CN(C)CCSC1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 XMRXKCIELMKQPF-UHFFFAOYSA-N 0.000 description 1
- JRTOLDFHNMOLDW-UHFFFAOYSA-N n,n-dimethyl-2-[3-(4-methylphenyl)quinolin-2-yl]sulfanylethanamine Chemical compound CN(C)CCSC1=NC2=CC=CC=C2C=C1C1=CC=C(C)C=C1 JRTOLDFHNMOLDW-UHFFFAOYSA-N 0.000 description 1
- UMJHMDLXUDUANE-UHFFFAOYSA-N n,n-dimethyl-3-(3-phenylquinolin-4-yl)sulfanylpropan-1-amine Chemical compound C1=NC2=CC=CC=C2C(SCCCN(C)C)=C1C1=CC=CC=C1 UMJHMDLXUDUANE-UHFFFAOYSA-N 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000002090 nicotinolytic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 210000000192 parasympathetic ganglia Anatomy 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 108700029318 rat female Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8117642 | 1981-06-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS425382A2 CS425382A2 (en) | 1984-02-13 |
| CS238624B2 true CS238624B2 (en) | 1985-12-16 |
Family
ID=10522379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS824253A CS238624B2 (en) | 1981-06-09 | 1982-06-08 | Production method of chinoline derivatives |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4435405A (el) |
| EP (1) | EP0066993B1 (el) |
| JP (1) | JPS58965A (el) |
| AR (1) | AR230437A1 (el) |
| AT (1) | ATE11534T1 (el) |
| AU (1) | AU556719B2 (el) |
| CA (1) | CA1189077A (el) |
| CS (1) | CS238624B2 (el) |
| DE (1) | DE3262122D1 (el) |
| DK (1) | DK152428C (el) |
| ES (3) | ES8401034A1 (el) |
| FI (1) | FI77451C (el) |
| GR (1) | GR76452B (el) |
| HU (1) | HU186523B (el) |
| IE (1) | IE53064B1 (el) |
| IL (1) | IL65852A (el) |
| IN (1) | IN158970B (el) |
| NO (1) | NO161066C (el) |
| NZ (1) | NZ200878A (el) |
| PH (1) | PH18503A (el) |
| PL (1) | PL135871B1 (el) |
| PT (1) | PT75024B (el) |
| SU (1) | SU1192618A3 (el) |
| YU (2) | YU43269B (el) |
| ZA (1) | ZA823586B (el) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE27152T1 (de) * | 1982-04-07 | 1987-05-15 | Ici Plc | Chinolin-derivate. |
| EP0093521B1 (en) * | 1982-05-04 | 1988-08-24 | Imperial Chemical Industries Plc | Quinoline derivatives |
| US4585866A (en) * | 1982-06-09 | 1986-04-29 | Merrell Dow Pharmaceuticals Inc. | Treatment of migraine with substituted tropyl benzoate derivatives |
| GB8308601D0 (en) * | 1983-03-29 | 1983-05-05 | Ici Plc | Heterocyclic compounds |
| JPS60166406A (ja) * | 1984-02-09 | 1985-08-29 | 株式会社イナックス | 乾式プレス装置の坏土充填方法 |
| GB8630071D0 (en) * | 1986-12-17 | 1987-01-28 | Glaxo Group Ltd | Medicaments |
| JP2733511B2 (ja) * | 1988-10-22 | 1998-03-30 | 日本臓器製薬株式会社 | 新規アミノアルカン誘導体 |
| JPH03147803A (ja) * | 1989-11-06 | 1991-06-24 | Tiger Mach Seisakusho:Kk | 表面多色変化模様のあるコンクリートブロックの製造方法 |
| FR2795645B1 (fr) * | 1999-06-30 | 2001-09-21 | Union Pharma Scient Appl | Nouvelle association pharmaceutique a activite analgesique |
| US6566361B2 (en) | 1999-06-30 | 2003-05-20 | Laboratories, Upsa | Azapirone pain treatment |
| EP1216988A4 (en) * | 1999-09-28 | 2005-04-20 | Nihon Nohyaku Co Ltd | THIOALKYLAMINE DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF |
| FR2810664B1 (fr) * | 2000-06-27 | 2004-12-24 | Adir | Nouveaux composes cyclopropaniques 1,1 et 1,2-dissubstitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| GB0306604D0 (en) * | 2003-03-21 | 2003-04-30 | Curidium Ltd | Second medical use |
| EP2129378B1 (en) | 2007-02-28 | 2011-06-01 | Thromboserin Limited | Therapeutic compositions comprising thromboserin or a salt thereof for use in the prevention or treatment of thrombosis in a patient at risk of bleeding |
| WO2009082268A2 (ru) | 2007-12-21 | 2009-07-02 | Alla Chem, Llc | ЛИГАНДЫ α-АДРЕНОЦЕПТОРОВ, ДОПАМИНОВЫХ, ГИСТАМИНОВЫХ, ИМИДАЗОЛИНОВЫХ И СЕРОТОНИНОВЫХ РЕЦЕПТОРОВ И ИХ ПРИМЕНЕНИЕ |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1049379B (de) | 1959-01-29 | Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-Bayerwerk | Verfahren zur Herstellung von 4 - (tert.-Aminoalkylmercapto)chinolinverbindungen | |
| DE430960C (de) | 1924-07-11 | 1926-06-23 | J G Farbenindustrie Akt Ges | Verfahren zur Darstellung von basischen AEthern von Chinolinderivaten |
| US1572768A (en) | 1925-06-26 | 1926-02-09 | Winthrop Chem Co Inc | Pharmaceutical product |
| US1860286A (en) | 1929-05-16 | 1932-05-24 | Soc Of Chemical Ind | Basic ethers of aryl-quinolines |
| GB1511390A (en) * | 1975-12-04 | 1978-05-17 | Pfizer Ltd | Imidazolylalkyl sulphide antifungal agents |
| US4343805A (en) | 1978-12-16 | 1982-08-10 | John Wyeth & Brother Limited | Heterocyclic compounds |
-
1982
- 1982-05-19 IN IN381/DEL/82A patent/IN158970B/en unknown
- 1982-05-20 AU AU83863/82A patent/AU556719B2/en not_active Expired
- 1982-05-21 AT AT82302607T patent/ATE11534T1/de not_active IP Right Cessation
- 1982-05-21 DE DE8282302607T patent/DE3262122D1/de not_active Expired
- 1982-05-21 EP EP82302607A patent/EP0066993B1/en not_active Expired
- 1982-05-23 IL IL65852A patent/IL65852A/xx not_active IP Right Cessation
- 1982-05-24 ZA ZA823586A patent/ZA823586B/xx unknown
- 1982-05-25 IE IE1243/82A patent/IE53064B1/en not_active IP Right Cessation
- 1982-05-26 US US06/382,116 patent/US4435405A/en not_active Expired - Lifetime
- 1982-05-27 GR GR68281A patent/GR76452B/el unknown
- 1982-05-28 PH PH27361A patent/PH18503A/en unknown
- 1982-06-02 FI FI821965A patent/FI77451C/fi not_active IP Right Cessation
- 1982-06-02 CA CA000404277A patent/CA1189077A/en not_active Expired
- 1982-06-07 HU HU821828A patent/HU186523B/hu unknown
- 1982-06-08 NO NO821904A patent/NO161066C/no not_active IP Right Cessation
- 1982-06-08 NZ NZ200878A patent/NZ200878A/en unknown
- 1982-06-08 YU YU1232/82A patent/YU43269B/xx unknown
- 1982-06-08 CS CS824253A patent/CS238624B2/cs unknown
- 1982-06-08 PL PL1982236836A patent/PL135871B1/pl unknown
- 1982-06-08 PT PT75024A patent/PT75024B/pt unknown
- 1982-06-08 JP JP57097043A patent/JPS58965A/ja active Granted
- 1982-06-08 SU SU823450275A patent/SU1192618A3/ru active
- 1982-06-09 ES ES512960A patent/ES8401034A1/es not_active Expired
- 1982-06-09 DK DK257782A patent/DK152428C/da not_active IP Right Cessation
-
1983
- 1983-01-14 ES ES519006A patent/ES519006A0/es active Granted
- 1983-08-30 AR AR294046A patent/AR230437A1/es active
- 1983-09-01 ES ES525298A patent/ES525298A0/es active Granted
-
1984
- 1984-11-08 YU YU1882/84A patent/YU42905B/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR880002232B1 (ko) | 퀴놀린 유도체와 그 염의 제조방법 | |
| AU659027B2 (en) | Substituted thienyl- or pyrrolylcarboxyclic acid derivatives, their preparation and medicines containing them | |
| CS238624B2 (en) | Production method of chinoline derivatives | |
| CN105518005A (zh) | 作为rock抑制剂的三环吡啶-甲酰胺衍生物 | |
| EP0482939A1 (en) | Isoquinolinone derivative | |
| KR19990028757A (ko) | 벤조[ｇ]퀴놀린 유도체 | |
| RU2191776C2 (ru) | Эрголиновые производные, способ их получения, фармацевтическая композиция | |
| FI100530B (fi) | Menetelmä substituoitujen diaminoftaali-imidien ja niiden analogien va lmistamiseksi | |
| WO2018084321A1 (ja) | Ｅｇｆｒ阻害及び腫瘍治療に有用な新規化合物 | |
| JP4865785B2 (ja) | Ｃｄｋ阻害剤としての置換１，５−ナフチリジンアゾリジノン | |
| JP2001512727A (ja) | ５ｈｔ−１受容体のリガンドとしてのニ環式化合物 | |
| WO2011127406A2 (en) | Acridines as inhibitors of haspin and dyrk kinases | |
| EP0093521B1 (en) | Quinoline derivatives | |
| JP3057095B2 (ja) | イサチン誘導体、その製造方法及びその使用方法 | |
| JP2959598B2 (ja) | 光学活性なチエノトリアゾロジアゼピン化合物 | |
| SI9011223A (en) | Indenoindole compounds | |
| CN100457737C (zh) | 喹啉酰胺衍生物、其制备方法和用途 | |
| DK162220B (da) | Tricykliske pyridazinderivater, som er agonister af cholinerge receptorer, fremgangsmaade til fremstilling af derivaterne, og laegemidler, hvori de er til stede | |
| CA2317515A1 (en) | Oxazole derivatives as serotonin-1a receptor agonists | |
| US4607040A (en) | Quinoline derivatives which are 5-hydroxytryptamine antagonists | |
| IE61028B1 (en) | Imidazole derivatives, process for their preparation and their use as alpha 2-adreno-receptor antagonists | |
| JP7110335B2 (ja) | プロテインキナーゼ阻害剤として有用なピリドキナゾリン誘導体 | |
| US6057340A (en) | Oxazole derivatives as serotonin-1A receptor agonists | |
| US4500708A (en) | Benzothiazine derivatives | |
| JPS59184162A (ja) | キノリン誘導体、その製造法及び該化合物を含有する、５―ヒドロキシトリプタミン桔抗質として使用する医薬組成物 |