CS241064B2 - Method of n-substituted nicotinamide's 1-oxide and its salts production - Google Patents
Method of n-substituted nicotinamide's 1-oxide and its salts production Download PDFInfo
- Publication number
- CS241064B2 CS241064B2 CS835876A CS587683A CS241064B2 CS 241064 B2 CS241064 B2 CS 241064B2 CS 835876 A CS835876 A CS 835876A CS 587683 A CS587683 A CS 587683A CS 241064 B2 CS241064 B2 CS 241064B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- formula
- substituted
- pharmaceutically acceptable
- chloride
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 22
- 150000003839 salts Chemical class 0.000 title claims description 16
- 239000011570 nicotinamide Substances 0.000 title description 13
- 229960003966 nicotinamide Drugs 0.000 title description 13
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 title description 3
- 235000005152 nicotinamide Nutrition 0.000 title description 2
- 150000005480 nicotinamides Chemical class 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- -1 N-substituted nicotinamide 1-oxide Chemical class 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- 239000011541 reaction mixture Substances 0.000 claims description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 150000008065 acid anhydrides Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 41
- 239000000047 product Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- 229910052739 hydrogen Inorganic materials 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 238000004458 analytical method Methods 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 229960001380 cimetidine Drugs 0.000 description 6
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 6
- VMXUWOKSQNHOCA-UKTHLTGXSA-N ranitidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-UKTHLTGXSA-N 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 230000002496 gastric effect Effects 0.000 description 5
- 229960001340 histamine Drugs 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
- 229960000620 ranitidine Drugs 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 230000001262 anti-secretory effect Effects 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N butenedioic acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- TVWVYAZWNFFFNV-UHFFFAOYSA-N 3-[3-[(3-methylpiperidin-1-yl)methyl]phenoxy]propan-1-amine Chemical compound C1C(C)CCCN1CC1=CC=CC(OCCCN)=C1 TVWVYAZWNFFFNV-UHFFFAOYSA-N 0.000 description 3
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- KPRZOPQOBJRYSW-UHFFFAOYSA-N o-hydroxybenzylamine Natural products NCC1=CC=CC=C1O KPRZOPQOBJRYSW-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- BHXFSLIKOQTDRU-UHFFFAOYSA-N 1-[(3-hydroxyphenyl)methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=CC(O)=C1 BHXFSLIKOQTDRU-UHFFFAOYSA-N 0.000 description 2
- WKRWITPEBNDNHB-UHFFFAOYSA-N 1-oxidopyridin-1-ium-3-carbonyl chloride Chemical compound [O-][N+]1=CC=CC(C(Cl)=O)=C1 WKRWITPEBNDNHB-UHFFFAOYSA-N 0.000 description 2
- VGJRNNIVMHRFAP-UHFFFAOYSA-N 1-oxidopyridin-1-ium-3-carbonyl chloride;hydrochloride Chemical compound Cl.[O-][N+]1=CC=CC(C(Cl)=O)=C1 VGJRNNIVMHRFAP-UHFFFAOYSA-N 0.000 description 2
- QXCOHSRHFCHCHN-UHFFFAOYSA-N 2-chloropyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(Cl)=C1 QXCOHSRHFCHCHN-UHFFFAOYSA-N 0.000 description 2
- BPUOHUMZZKDGLM-UHFFFAOYSA-N 3-[3-(morpholin-4-ylmethyl)phenoxy]propan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCOCC2)=C1 BPUOHUMZZKDGLM-UHFFFAOYSA-N 0.000 description 2
- AUZJNNGWUPVISA-UHFFFAOYSA-N 3-[4-[(dimethylamino)methyl]pyridin-2-yl]oxypropan-1-amine Chemical compound CN(C)CC1=CC=NC(OCCCN)=C1 AUZJNNGWUPVISA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- LTFPRTSTYUPEST-UHFFFAOYSA-N C1=CNC(CCCOC=2N=CC=CC=2)=C1CN Chemical compound C1=CNC(CCCOC=2N=CC=CC=2)=C1CN LTFPRTSTYUPEST-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 102000000543 Histamine Receptors Human genes 0.000 description 2
- 108010002059 Histamine Receptors Proteins 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 235000011087 fumaric acid Nutrition 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- FJCFFCXMEXZEIM-UHFFFAOYSA-N oxiniacic acid Chemical compound OC(=O)C1=CC=C[N+]([O-])=C1 FJCFFCXMEXZEIM-UHFFFAOYSA-N 0.000 description 2
- XAHFWXWXESMIPV-UHFFFAOYSA-N oxmetidine Chemical compound CC1=NC=N[C]1CSCCNC(NC1=O)=NC=C1CC1=CC=C(OCO2)C2=C1 XAHFWXWXESMIPV-UHFFFAOYSA-N 0.000 description 2
- 229950006792 oxmetidine Drugs 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- UIKROCXWUNQSPJ-VIFPVBQESA-N (-)-cotinine Chemical compound C1CC(=O)N(C)[C@@H]1C1=CC=CN=C1 UIKROCXWUNQSPJ-VIFPVBQESA-N 0.000 description 1
- WWAHCEQEEDQIPJ-UHFFFAOYSA-N (4-nitrophenyl) 1-oxidopyridin-1-ium-3-carboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)C1=CC=C[N+]([O-])=C1 WWAHCEQEEDQIPJ-UHFFFAOYSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- IOXVYMZUWXVQHF-UHFFFAOYSA-N 1-[2-[3-(2,5-dimethylpyrrol-1-yl)propoxy]pyridin-4-yl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=NC(OCCCN2C(=CC=C2C)C)=C1 IOXVYMZUWXVQHF-UHFFFAOYSA-N 0.000 description 1
- KEDVUOWPLAHMLZ-UHFFFAOYSA-N 1-cyano-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-2-prop-2-ynylguanidine Chemical compound CC=1NC=NC=1CSCCNC(NC#N)=NCC#C KEDVUOWPLAHMLZ-UHFFFAOYSA-N 0.000 description 1
- YDDXVAXDYKBWDX-UHFFFAOYSA-N 1-cyano-3-[2-[[2-(diaminomethylideneamino)-4-thiazolyl]methylthio]ethyl]-2-methylguanidine Chemical compound N#CNC(=NC)NCCSCC1=CSC(N=C(N)N)=N1 YDDXVAXDYKBWDX-UHFFFAOYSA-N 0.000 description 1
- HTJLEPZHNSTLDH-UHFFFAOYSA-N 1-oxido-n-[3-[3-(pyrrolidin-1-ylmethyl)phenoxy]propyl]pyridin-1-ium-3-carboxamide Chemical compound [O-][N+]1=CC=CC(C(=O)NCCCOC=2C=C(CN3CCCC3)C=CC=2)=C1 HTJLEPZHNSTLDH-UHFFFAOYSA-N 0.000 description 1
- UFUJBDFTFIGERB-UHFFFAOYSA-N 1-oxido-n-[3-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropyl]pyridin-1-ium-3-carboxamide Chemical compound [O-][N+]1=CC=CC(C(=O)NCCCOC=2N=CC=C(CN3CCCCC3)C=2)=C1 UFUJBDFTFIGERB-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- ZGXGVSMGAUWMFP-UHFFFAOYSA-N 2-[1-[[4-(3-aminopropoxy)phenyl]methyl]piperazin-2-yl]ethanol Chemical compound C1=CC(OCCCN)=CC=C1CN1C(CCO)CNCC1 ZGXGVSMGAUWMFP-UHFFFAOYSA-N 0.000 description 1
- FBGQINAIDCSUHA-UHFFFAOYSA-N 2-[4-[2-(3-aminopropoxy)phenyl]-2-methylpiperazin-1-yl]ethanol Chemical compound C1CN(CCO)C(C)CN1C1=CC=CC=C1OCCCN FBGQINAIDCSUHA-UHFFFAOYSA-N 0.000 description 1
- WSQRUKJFFKJPFA-UHFFFAOYSA-N 2-[[2-(3-aminopropoxy)phenyl]methylamino]ethanol Chemical compound NCCCOC1=CC=CC=C1CNCCO WSQRUKJFFKJPFA-UHFFFAOYSA-N 0.000 description 1
- WSLAJZPKKCKUDK-UHFFFAOYSA-N 2-chloro-n,n-dimethylpyridine-4-carboxamide Chemical compound CN(C)C(=O)C1=CC=NC(Cl)=C1 WSLAJZPKKCKUDK-UHFFFAOYSA-N 0.000 description 1
- NPRZWOJTSGFSBF-UHFFFAOYSA-N 2-chloropyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC(Cl)=C1 NPRZWOJTSGFSBF-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- MYUAAKUXSYMYLR-UHFFFAOYSA-N 3-(2,5-dimethyl-1h-pyrrol-3-yl)propan-1-ol Chemical compound CC1=CC(CCCO)=C(C)N1 MYUAAKUXSYMYLR-UHFFFAOYSA-N 0.000 description 1
- WBHXWMIFIZMHKS-UHFFFAOYSA-N 3-(morpholin-4-ylmethyl)phenol Chemical compound OC1=CC=CC(CN2CCOCC2)=C1 WBHXWMIFIZMHKS-UHFFFAOYSA-N 0.000 description 1
- FVGIVIALEYCTBF-UHFFFAOYSA-N 3-[2-[(1-cyclopropylethylamino)methyl]phenoxy]propan-1-amine Chemical compound C1CC1C(C)NCC1=CC=CC=C1OCCCN FVGIVIALEYCTBF-UHFFFAOYSA-N 0.000 description 1
- COWOOVKQLRGXDS-UHFFFAOYSA-N 3-[2-[(3,4,5-trimethylpiperazin-1-yl)methyl]phenoxy]propan-1-amine Chemical compound C1C(C)N(C)C(C)CN1CC1=CC=CC=C1OCCCN COWOOVKQLRGXDS-UHFFFAOYSA-N 0.000 description 1
- JTGBVNREFCCNPA-UHFFFAOYSA-N 3-[2-[(3,4-dimethylpiperazin-1-yl)methyl]phenoxy]propan-1-amine Chemical compound C1CN(C)C(C)CN1CC1=CC=CC=C1OCCCN JTGBVNREFCCNPA-UHFFFAOYSA-N 0.000 description 1
- LDWRLCRCPGDPIO-UHFFFAOYSA-N 3-[2-[(3,5-dimethylpiperidin-1-yl)methyl]phenoxy]propan-1-amine Chemical compound C1C(C)CC(C)CN1CC1=CC=CC=C1OCCCN LDWRLCRCPGDPIO-UHFFFAOYSA-N 0.000 description 1
- UHLFKWQPBVSWPH-UHFFFAOYSA-N 3-[3-(1-piperidin-1-ylethyl)phenoxy]propan-1-amine Chemical compound C=1C=CC(OCCCN)=CC=1C(C)N1CCCCC1 UHLFKWQPBVSWPH-UHFFFAOYSA-N 0.000 description 1
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- FPGRZISJRZAYDE-UHFFFAOYSA-N 3-[3-[(dipropylamino)methyl]phenoxy]propan-1-amine Chemical compound CCCN(CCC)CC1=CC=CC(OCCCN)=C1 FPGRZISJRZAYDE-UHFFFAOYSA-N 0.000 description 1
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- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
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- CQAIHQCQSXQYFC-UHFFFAOYSA-N oxalic acid 1-oxido-N-[3-[3-(pyrrolidin-1-ylmethyl)phenoxy]propyl]pyridin-1-ium-3-carboxamide Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O.OC(=O)C(O)=O.[O-][n+]1cccc(c1)C(=O)NCCCOc1cccc(CN2CCCC2)c1.[O-][n+]1cccc(c1)C(=O)NCCCOc1cccc(CN2CCCC2)c1 CQAIHQCQSXQYFC-UHFFFAOYSA-N 0.000 description 1
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- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- 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
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8214128A FR2531704B1 (fr) | 1982-08-13 | 1982-08-13 | Amides d'acides (hetero)aromatiques n-substitues, leurs sels, procede pour leur preparation et compositions pharmaceutiques en contenant |
| FR8306681A FR2544717B1 (fr) | 1983-04-22 | 1983-04-22 | Nicotinamide l-oxyde n-substitue, ses sels, procede pour leur preparation et compositions pharmaceutiques en contenant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS587683A2 CS587683A2 (en) | 1985-07-16 |
| CS241064B2 true CS241064B2 (en) | 1986-03-13 |
Family
ID=26223047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS835876A CS241064B2 (en) | 1982-08-13 | 1983-08-10 | Method of n-substituted nicotinamide's 1-oxide and its salts production |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4514408A (el) |
| EP (1) | EP0101380A3 (el) |
| AU (1) | AU556247B2 (el) |
| CA (1) | CA1209995A (el) |
| CS (1) | CS241064B2 (el) |
| DD (1) | DD213921A5 (el) |
| DK (1) | DK367683A (el) |
| FI (1) | FI832919A (el) |
| GR (1) | GR78927B (el) |
| HU (1) | HU191869B (el) |
| IL (1) | IL69392A (el) |
| MA (1) | MA19871A1 (el) |
| NO (1) | NO832894L (el) |
| NZ (1) | NZ205239A (el) |
| OA (1) | OA07521A (el) |
| PH (1) | PH19511A (el) |
| PL (1) | PL141540B1 (el) |
| PT (1) | PT77192B (el) |
| SU (1) | SU1212323A3 (el) |
| YU (1) | YU169083A (el) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4764598A (en) * | 1985-08-22 | 1988-08-16 | The United States Of America As Represented By The Department Of Energy | Precursors to radiopharmaceutical agents for tissue imaging |
| MA20552A1 (fr) * | 1985-10-11 | 1986-07-01 | Pan Medica Sa | Alkylacarboxamides de pyridylalkylamines,leurs preparations et leurs utilisations |
| US4994456A (en) * | 1989-03-01 | 1991-02-19 | Nisshin Flour Milling Co., Ltd. | Pyridinecarboxylic acid amide derivatives and pharmaceutical compositions comprising same |
| EP0569587A1 (en) * | 1991-01-30 | 1993-11-18 | Central Glass Company, Limited | Phthalimide compound and production thereof |
| DE69219354T2 (de) * | 1991-05-10 | 1997-10-23 | Takeda Chemical Industries Ltd | Pyridinderivate, deren Herstellung und Anwendung |
| JP2008542365A (ja) * | 2005-05-31 | 2008-11-27 | アストラゼネカ・アクチエボラーグ | 新規なｍｃｈｒ１アンタゴニスト並びにｍｃｈｒ１媒介状態及び障害の処置のためのそれらの使用 |
| EP4196793A1 (en) | 2020-08-11 | 2023-06-21 | Université de Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
| CN114523832B (zh) * | 2020-11-19 | 2023-12-22 | 本田技研工业(中国)投资有限公司 | 一种电池保护装置、车辆及电池保护装置的安装方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL286303A (el) * | 1961-12-06 | |||
| JPS568352A (en) * | 1979-07-03 | 1981-01-28 | Shionogi & Co Ltd | Aminoalkylvenzene derivative |
| US4293557A (en) * | 1979-07-03 | 1981-10-06 | Teikoku Hormone Mfg. Co., Ltd. | Antiulcer phenoxypropylamine derivatives |
-
1983
- 1983-08-01 IL IL69392A patent/IL69392A/xx unknown
- 1983-08-09 PH PH29372A patent/PH19511A/en unknown
- 1983-08-09 AU AU17807/83A patent/AU556247B2/en not_active Ceased
- 1983-08-10 EP EP83401638A patent/EP0101380A3/fr not_active Ceased
- 1983-08-10 CS CS835876A patent/CS241064B2/cs unknown
- 1983-08-11 HU HU832829A patent/HU191869B/hu unknown
- 1983-08-11 GR GR72198A patent/GR78927B/el unknown
- 1983-08-12 DK DK367683A patent/DK367683A/da not_active Application Discontinuation
- 1983-08-12 PT PT77192A patent/PT77192B/pt unknown
- 1983-08-12 SU SU833634875A patent/SU1212323A3/ru active
- 1983-08-12 PL PL1983243410A patent/PL141540B1/pl unknown
- 1983-08-12 NO NO832894A patent/NO832894L/no unknown
- 1983-08-12 NZ NZ205239A patent/NZ205239A/en unknown
- 1983-08-12 US US06/522,749 patent/US4514408A/en not_active Expired - Fee Related
- 1983-08-12 CA CA000434507A patent/CA1209995A/fr not_active Expired
- 1983-08-12 FI FI832919A patent/FI832919A/fi not_active Application Discontinuation
- 1983-08-12 YU YU01690/83A patent/YU169083A/xx unknown
- 1983-08-12 MA MA20093A patent/MA19871A1/fr unknown
- 1983-08-12 OA OA58088A patent/OA07521A/xx unknown
- 1983-08-12 DD DD83253927A patent/DD213921A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU1780783A (en) | 1984-02-16 |
| YU169083A (en) | 1986-12-31 |
| PH19511A (en) | 1986-05-14 |
| PL141540B1 (en) | 1987-08-31 |
| PL243410A1 (en) | 1985-05-07 |
| CA1209995A (fr) | 1986-08-19 |
| EP0101380A3 (fr) | 1985-10-16 |
| CS587683A2 (en) | 1985-07-16 |
| FI832919A (fi) | 1984-02-14 |
| PT77192A (fr) | 1983-09-01 |
| US4514408A (en) | 1985-04-30 |
| IL69392A0 (en) | 1983-11-30 |
| OA07521A (fr) | 1985-03-31 |
| IL69392A (en) | 1987-01-30 |
| NZ205239A (en) | 1985-09-13 |
| DD213921A5 (de) | 1984-09-26 |
| EP0101380A2 (fr) | 1984-02-22 |
| DK367683A (da) | 1984-02-14 |
| NO832894L (no) | 1984-02-14 |
| GR78927B (el) | 1984-10-02 |
| DK367683D0 (da) | 1983-08-12 |
| MA19871A1 (fr) | 1984-04-01 |
| HU191869B (en) | 1987-04-28 |
| AU556247B2 (en) | 1986-10-30 |
| PT77192B (fr) | 1986-02-03 |
| FI832919A0 (fi) | 1983-08-12 |
| SU1212323A3 (ru) | 1986-02-15 |
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