CA1223257A - Compounds active in the treatment of ulcer and allergic skin symptoms - Google Patents
Compounds active in the treatment of ulcer and allergic skin symptomsInfo
- Publication number
- CA1223257A CA1223257A CA000438490A CA438490A CA1223257A CA 1223257 A CA1223257 A CA 1223257A CA 000438490 A CA000438490 A CA 000438490A CA 438490 A CA438490 A CA 438490A CA 1223257 A CA1223257 A CA 1223257A
- Authority
- CA
- Canada
- Prior art keywords
- dimethylamino
- thio
- methyl
- furfuryl
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 73
- 208000025865 Ulcer Diseases 0.000 title abstract description 6
- 231100000397 ulcer Toxicity 0.000 title abstract description 6
- 230000000172 allergic effect Effects 0.000 title abstract description 4
- 208000010668 atopic eczema Diseases 0.000 title abstract description 4
- 208000024891 symptom Diseases 0.000 title abstract description 4
- WXEHBUMAEPOYKP-UHFFFAOYSA-N methylsulfanylethane Chemical compound CCSC WXEHBUMAEPOYKP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 24
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims description 101
- -1 piperidino, 4-methylpiperidino Chemical group 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 32
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 24
- JKRUSMLUQVGEAP-UHFFFAOYSA-N n,n-dimethyl-1-[5-(2-methylsulfanylethylsulfanylmethyl)furan-2-yl]methanamine Chemical compound CSCCSCC1=CC=C(CN(C)C)O1 JKRUSMLUQVGEAP-UHFFFAOYSA-N 0.000 claims description 17
- 229910021529 ammonia Inorganic materials 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- RZUDRRXSEJRTQY-UHFFFAOYSA-N 1-(4-methylpiperidin-1-yl)-2-nitroethenamine Chemical compound CC1CCN(C(N)=C[N+]([O-])=O)CC1 RZUDRRXSEJRTQY-UHFFFAOYSA-N 0.000 claims description 2
- KYWOXJAUDNZQRA-UHFFFAOYSA-N 1-morpholin-4-yl-2-nitroethenamine Chemical compound [O-][N+](=O)C=C(N)N1CCOCC1 KYWOXJAUDNZQRA-UHFFFAOYSA-N 0.000 claims description 2
- CYCGKMWHXBWMRM-UHFFFAOYSA-N 1-n'-(azepan-1-yl)-2-nitroethene-1,1-diamine Chemical compound [O-][N+](=O)C=C(N)NN1CCCCCC1 CYCGKMWHXBWMRM-UHFFFAOYSA-N 0.000 claims description 2
- ASWXSZFDNKRBFB-UHFFFAOYSA-N 1-n'-cyclohexa-1,4-dien-1-yl-2-nitroethene-1,1-diamine Chemical compound [O-][N+](=O)C=C(N)NC1=CCC=CC1 ASWXSZFDNKRBFB-UHFFFAOYSA-N 0.000 claims description 2
- MSYBMQREJYVMHZ-UHFFFAOYSA-N 1-n'-cyclopentyl-2-nitroethene-1,1-diamine Chemical compound [O-][N+](=O)C=C(N)NC1CCCC1 MSYBMQREJYVMHZ-UHFFFAOYSA-N 0.000 claims description 2
- DNINUKCIPWSQMA-UHFFFAOYSA-N 2-nitro-1-piperidin-1-ylethenamine Chemical compound [O-][N+](=O)C=C(N)N1CCCCC1 DNINUKCIPWSQMA-UHFFFAOYSA-N 0.000 claims description 2
- XJMNCSRHVMDXNL-UHFFFAOYSA-N 2-nitro-1-pyrrolidin-1-ylethenamine Chemical compound [O-][N+](=O)C=C(N)N1CCCC1 XJMNCSRHVMDXNL-UHFFFAOYSA-N 0.000 claims description 2
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 claims description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 claims description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 20
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 claims 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- LSYCIOKMMYUZMX-UHFFFAOYSA-N 1-(4-benzylpiperidin-1-yl)-2-nitroethenamine Chemical compound C1CN(C(=C[N+]([O-])=O)N)CCC1CC1=CC=CC=C1 LSYCIOKMMYUZMX-UHFFFAOYSA-N 0.000 claims 1
- HFYLIBVGAWJGNQ-UHFFFAOYSA-N 1-(azepan-1-yl)ethenamine Chemical compound NC(=C)N1CCCCCC1 HFYLIBVGAWJGNQ-UHFFFAOYSA-N 0.000 claims 1
- YQTPOLOEXQLOGY-UHFFFAOYSA-N 1-n'-(1-ethylpiperidin-2-yl)-2-nitroethene-1,1-diamine Chemical compound CCN1CCCCC1NC(N)=C[N+]([O-])=O YQTPOLOEXQLOGY-UHFFFAOYSA-N 0.000 claims 1
- JXQFWNNEMLNRCV-UHFFFAOYSA-N 1-n'-(azepan-1-yl)-1-n-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-2-nitroethene-1,1-diamine Chemical compound O1C(CN(C)C)=CC=C1CSCCNC(=C[N+]([O-])=O)NN1CCCCCC1 JXQFWNNEMLNRCV-UHFFFAOYSA-N 0.000 claims 1
- YSIJRAWNBCPVOV-UHFFFAOYSA-N 1-n'-cycloheptyl-1-n-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-2-nitroethene-1,1-diamine Chemical compound O1C(CN(C)C)=CC=C1CSCCNC(=C[N+]([O-])=O)NC1CCCCCC1 YSIJRAWNBCPVOV-UHFFFAOYSA-N 0.000 claims 1
- IJCPGHIDEIVIBY-UHFFFAOYSA-N 1-n'-cycloheptyl-2-nitroethene-1,1-diamine Chemical compound [O-][N+](=O)C=C(N)NC1CCCCCC1 IJCPGHIDEIVIBY-UHFFFAOYSA-N 0.000 claims 1
- ODHRVQTXERBFCH-UHFFFAOYSA-N 1-n'-cyclopentyl-1-n-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-2-nitroethene-1,1-diamine Chemical compound O1C(CN(C)C)=CC=C1CSCCNC(=C[N+]([O-])=O)NC1CCCC1 ODHRVQTXERBFCH-UHFFFAOYSA-N 0.000 claims 1
- XKBGOFIASRVHAR-UHFFFAOYSA-N 2-[4-(1-amino-2-nitroethenyl)piperazin-1-yl]ethanol Chemical compound [O-][N+](=O)C=C(N)N1CCN(CCO)CC1 XKBGOFIASRVHAR-UHFFFAOYSA-N 0.000 claims 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 239000005557 antagonist Substances 0.000 abstract description 2
- 102000003710 Histamine H2 Receptors Human genes 0.000 abstract 1
- 108090000050 Histamine H2 Receptors Proteins 0.000 abstract 1
- 239000000047 product Substances 0.000 description 40
- 238000004458 analytical method Methods 0.000 description 35
- 239000000155 melt Substances 0.000 description 31
- 239000000203 mixture Substances 0.000 description 22
- 241001465754 Metazoa Species 0.000 description 21
- 241000700159 Rattus Species 0.000 description 19
- 238000009738 saturating Methods 0.000 description 13
- 230000000694 effects Effects 0.000 description 10
- 241000282472 Canis lupus familiaris Species 0.000 description 8
- 230000002496 gastric effect Effects 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical group CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 6
- 229960000620 ranitidine Drugs 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
- 238000012453 sprague-dawley rat model Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 108010012944 Tetragastrin Proteins 0.000 description 4
- 229960001380 cimetidine Drugs 0.000 description 4
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RGYLYUZOGHTBRF-BIHRQFPBSA-N tetragastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C2=CC=CC=C2NC=1)CCSC)C(N)=O)C1=CC=CC=C1 RGYLYUZOGHTBRF-BIHRQFPBSA-N 0.000 description 4
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 231100001048 fetal toxicity Toxicity 0.000 description 3
- IOPLHGOSNCJOOO-UHFFFAOYSA-N methyl 3,4-diaminobenzoate Chemical class COC(=O)C1=CC=C(N)C(N)=C1 IOPLHGOSNCJOOO-UHFFFAOYSA-N 0.000 description 3
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical compound [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- ZERULLAPCVRMCO-UHFFFAOYSA-N sulfure de di n-propyle Natural products CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 3
- 206010020601 Hyperchlorhydria Diseases 0.000 description 2
- 241001024304 Mino Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- 208000008469 Peptic Ulcer Diseases 0.000 description 2
- 208000003251 Pruritus Diseases 0.000 description 2
- 208000007107 Stomach Ulcer Diseases 0.000 description 2
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000000767 anti-ulcer Effects 0.000 description 2
- 230000002425 cardiocirculatory effect Effects 0.000 description 2
- 230000027326 copulation Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- MXCPYJZDGPQDRA-UHFFFAOYSA-N dialuminum;2-acetyloxybenzoic acid;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3].CC(=O)OC1=CC=CC=C1C(O)=O MXCPYJZDGPQDRA-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000002489 hematologic effect Effects 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 208000011906 peptic ulcer disease Diseases 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 230000007666 subchronic toxicity Effects 0.000 description 2
- 231100000195 subchronic toxicity Toxicity 0.000 description 2
- 238000011287 therapeutic dose Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- TVSWGZXTOIDLKR-UHFFFAOYSA-N 1-(azepan-1-yl)-2-nitroethenamine Chemical compound [O-][N+](=O)C=C(N)N1CCCCCC1 TVSWGZXTOIDLKR-UHFFFAOYSA-N 0.000 description 1
- WAKUKXKZEXFXJP-UHFFFAOYSA-N 1-ethylpiperidin-3-amine Chemical compound CCN1CCCC(N)C1 WAKUKXKZEXFXJP-UHFFFAOYSA-N 0.000 description 1
- LPVHXJZBOLEAQG-UHFFFAOYSA-N 1-n'-(3-bicyclo[2.2.1]hept-2-enyl)-2-nitroethene-1,1-diamine Chemical compound C1CC2C(NC(N)=C[N+]([O-])=O)=CC1C2 LPVHXJZBOLEAQG-UHFFFAOYSA-N 0.000 description 1
- PNPUEIWCJJPATO-UHFFFAOYSA-N 1-n'-cyclohexyl-2-nitroethene-1,1-diamine Chemical compound [O-][N+](=O)C=C(N)NC1CCCCC1 PNPUEIWCJJPATO-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 241000736839 Chara Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000700110 Myocastor coypus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- UGBKOURNNQREPE-UHFFFAOYSA-N azepan-1-amine Chemical compound NN1CCCCCC1 UGBKOURNNQREPE-UHFFFAOYSA-N 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000132 chronic toxicity testing Toxicity 0.000 description 1
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 1
- ITIUJKMFPOKOKN-UHFFFAOYSA-N cyclohexa-1,4-dien-1-amine Chemical compound NC1=CCC=CC1 ITIUJKMFPOKOKN-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- NXLOLUFNDSBYTP-UHFFFAOYSA-N retene Chemical compound C1=CC=C2C3=CC=C(C(C)C)C=C3C=CC2=C1C NXLOLUFNDSBYTP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000007939 sustained release tablet Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- 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
- C07D295/12—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 or doubly bound nitrogen atoms
- C07D295/125—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- 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
- A61P17/00—Drugs for dermatological disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no 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 the ring nitrogen atom
- C07D203/12—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- 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
- C07D211/56—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20954/82A IT1190793B (it) | 1982-04-27 | 1982-04-27 | Composti attivi nel trattamento dell'ulcera e sintomi allergici della pelle |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1223257A true CA1223257A (en) | 1987-06-23 |
Family
ID=11174566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000438490A Expired CA1223257A (en) | 1982-04-27 | 1983-10-06 | Compounds active in the treatment of ulcer and allergic skin symptoms |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4613596A (en, 2012) |
| EP (1) | EP0092647B1 (en, 2012) |
| JP (1) | JPS6081177A (en, 2012) |
| AT (1) | ATE24904T1 (en, 2012) |
| AU (1) | AU563738B2 (en, 2012) |
| CA (1) | CA1223257A (en, 2012) |
| DE (1) | DE3369135D1 (en, 2012) |
| IT (1) | IT1190793B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1196133B (it) * | 1984-06-06 | 1988-11-10 | Ausonia Farma Srl | Derivati furanici con attivita' antiulcera |
| IT1180185B (it) * | 1984-06-12 | 1987-09-23 | Magis Farmaceutici | Derivato della ranitidina utile nel trattamento dell'ulcera |
| US4707550A (en) * | 1986-04-28 | 1987-11-17 | Ortho Pharmaceutical Corporation | N-(substituted thienyl)-N'-(substituted piperazinyl)-ureas |
| IL100688A (en) * | 1987-08-01 | 1995-08-31 | Takeda Chemical Industries Ltd | Intermediates for the production of unsaturated amines in position A and the process for their preparation |
| GB9009437D0 (en) * | 1990-04-26 | 1990-06-20 | Glaxo Group Ltd | Chemical compounds |
| CA2189964A1 (en) * | 1994-05-18 | 1995-11-23 | Haruhiko Kikuchi | Novel diaminomethylidene derivative |
| US6248785B1 (en) | 1996-08-06 | 2001-06-19 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6177448B1 (en) | 1996-08-06 | 2001-01-23 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| EP1116486A4 (en) * | 1998-09-22 | 2007-06-20 | Ishihara Sangyo Kaisha | MEDICAL COMPOSITION CONTAINING NITROETHENAMINE DERIVATIVES OR SALTS AS ACTIVE INGREDIENTS |
| KR20080035702A (ko) | 2002-01-11 | 2008-04-23 | 상꾜 가부시키가이샤 | 아미노 알코올 유도체 또는 포스폰산 유도체 및 이들을함유하는 의약 조성물 |
| CN1921847B (zh) | 2004-02-24 | 2010-06-16 | 三共株式会社 | 氨基醇化合物 |
| US20230349922A1 (en) | 2020-08-11 | 2023-11-02 | Université De Strasbourg | H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4233302A (en) * | 1977-12-23 | 1980-11-11 | Glaxo Group Limited | Amine derivatives and pharmaceutical compositions containing them |
| US4287346A (en) * | 1979-02-16 | 1981-09-01 | Eisai Co., Ltd. | Cyanoguanidine derivatives |
| EP0057981A3 (en) * | 1981-02-09 | 1982-08-25 | Beecham Group Plc | Aromatic compounds, processes for their preparation and their use |
-
1982
- 1982-04-27 IT IT20954/82A patent/IT1190793B/it active
-
1983
- 1983-02-03 AT AT83100992T patent/ATE24904T1/de not_active IP Right Cessation
- 1983-02-03 DE DE8383100992T patent/DE3369135D1/de not_active Expired
- 1983-02-03 EP EP83100992A patent/EP0092647B1/en not_active Expired
- 1983-09-29 AU AU19760/83A patent/AU563738B2/en not_active Ceased
- 1983-10-03 JP JP58183243A patent/JPS6081177A/ja active Granted
- 1983-10-06 CA CA000438490A patent/CA1223257A/en not_active Expired
-
1985
- 1985-12-16 US US06/808,375 patent/US4613596A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IT8220954A0 (it) | 1982-04-27 |
| EP0092647A1 (en) | 1983-11-02 |
| JPH0429671B2 (en, 2012) | 1992-05-19 |
| AU563738B2 (en) | 1987-07-23 |
| IT1190793B (it) | 1988-02-24 |
| AU1976083A (en) | 1985-04-04 |
| JPS6081177A (ja) | 1985-05-09 |
| DE3369135D1 (en) | 1987-02-19 |
| EP0092647B1 (en) | 1987-01-14 |
| US4613596A (en) | 1986-09-23 |
| ATE24904T1 (de) | 1987-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |