CH627463A5 - Salts of basic amino sugars or of basic amino acids - Google Patents
Salts of basic amino sugars or of basic amino acids Download PDFInfo
- Publication number
- CH627463A5 CH627463A5 CH80978A CH80978A CH627463A5 CH 627463 A5 CH627463 A5 CH 627463A5 CH 80978 A CH80978 A CH 80978A CH 80978 A CH80978 A CH 80978A CH 627463 A5 CH627463 A5 CH 627463A5
- Authority
- CH
- Switzerland
- Prior art keywords
- radical
- oxo
- basic amino
- benzopyran
- carboxylic acid
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 19
- 150000002337 glycosamines Chemical class 0.000 title claims description 13
- 150000001413 amino acids Chemical class 0.000 title claims description 11
- -1 amino, amino Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000012153 distilled water Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 9
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 4
- 239000004472 Lysine Substances 0.000 claims description 4
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 4
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229960003104 ornithine Drugs 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 3
- 239000004475 Arginine Substances 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229960002442 glucosamine Drugs 0.000 claims description 3
- 230000001698 pyrogenic effect Effects 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 239000002198 insoluble material Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- LVOICKNPHXSSQM-UHFFFAOYSA-N prop-2-en-1-one Chemical compound C=C[C]=O LVOICKNPHXSSQM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 206010002198 Anaphylactic reaction Diseases 0.000 description 12
- 230000036783 anaphylactic response Effects 0.000 description 12
- 208000003455 anaphylaxis Diseases 0.000 description 12
- 235000001014 amino acid Nutrition 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- 210000003405 ileum Anatomy 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- RVTVXPWEBXGABP-UHFFFAOYSA-N 7-[2-hydroxy-3-(2-propylphenoxy)propoxy]-4-oxo-8-propylchromene-2-carboxylic acid Chemical compound CCCC1=CC=CC=C1OCC(O)COC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1CCC RVTVXPWEBXGABP-UHFFFAOYSA-N 0.000 description 2
- JHAGRZFIEACDNG-UHFFFAOYSA-N 7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-4-oxo-8-propylchromene-2-carboxylic acid Chemical compound C1=CC(C(C)=O)=C(O)C(CCC)=C1OCCCOC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1CCC JHAGRZFIEACDNG-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 108010058846 Ovalbumin Proteins 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 150000001562 benzopyrans Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 235000018977 lysine Nutrition 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- JXYWFNAQESKDNC-BTJKTKAUSA-N (z)-4-hydroxy-4-oxobut-2-enoate;2-[(4-methoxyphenyl)methyl-pyridin-2-ylamino]ethyl-dimethylazanium Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 JXYWFNAQESKDNC-BTJKTKAUSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FZGDNLVOMOSEND-UHFFFAOYSA-N 4-oxo-7-[3-(2-propylphenoxy)propoxy]chromene-2-carboxylic acid Chemical compound CCCC1=CC=CC=C1OCCCOC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 FZGDNLVOMOSEND-UHFFFAOYSA-N 0.000 description 1
- OCINTJGCUFLFGD-UHFFFAOYSA-N 4-oxo-7-[5-(2-propylphenoxy)pentoxy]chromene-2-carboxylic acid Chemical compound CCCC1=CC=CC=C1OCCCCCOC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 OCINTJGCUFLFGD-UHFFFAOYSA-N 0.000 description 1
- GAAQTRGKCRMQTH-UHFFFAOYSA-N 4-oxo-7-[5-(3-phenylmethoxyphenoxy)pentoxy]chromene-2-carboxylic acid Chemical compound C1=C2OC(C(=O)O)=CC(=O)C2=CC=C1OCCCCCOC(C=1)=CC=CC=1OCC1=CC=CC=C1 GAAQTRGKCRMQTH-UHFFFAOYSA-N 0.000 description 1
- MRBOBKQEMKXFAK-UHFFFAOYSA-N 4-oxo-7-[5-(4-oxochromen-7-yl)oxypentoxy]chromene-2-carboxylic acid Chemical compound O1C=CC(=O)C=2C1=CC(OCCCCCOC1=CC=C3C(=O)C=C(OC3=C1)C(=O)O)=CC=2 MRBOBKQEMKXFAK-UHFFFAOYSA-N 0.000 description 1
- WPEXAQBFJCJIFG-UHFFFAOYSA-N 4-oxo-8-propyl-7-[3-(2-propylphenoxy)propoxy]chromene-2-carboxylic acid Chemical compound CCCC1=CC=CC=C1OCCCOC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1CCC WPEXAQBFJCJIFG-UHFFFAOYSA-N 0.000 description 1
- NDRRZOPLBYZKGU-UHFFFAOYSA-N 5-[2-hydroxy-3-(2-propylphenoxy)propoxy]-4-oxochromene-2-carboxylic acid Chemical compound CCCC1=CC=CC=C1OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 NDRRZOPLBYZKGU-UHFFFAOYSA-N 0.000 description 1
- OYVBNQQAAFDLOR-UHFFFAOYSA-N 5-[2-hydroxy-3-(4-oxochromen-5-yl)oxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=CO2 OYVBNQQAAFDLOR-UHFFFAOYSA-N 0.000 description 1
- QETJQWNWGMQYEW-UHFFFAOYSA-N 5-[3-(2-acetyl-3-hydroxyphenoxy)-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound CC(=O)C1=C(O)C=CC=C1OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 QETJQWNWGMQYEW-UHFFFAOYSA-N 0.000 description 1
- FOZTVQQGHHPQRJ-UHFFFAOYSA-N 5-[3-[2-[3-(dimethylamino)prop-2-enoyl]-3-hydroxyphenoxy]-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound CN(C)C=CC(=O)C1=C(O)C=CC=C1OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 FOZTVQQGHHPQRJ-UHFFFAOYSA-N 0.000 description 1
- KKQCOMIWROCVST-UHFFFAOYSA-N 6-[2-hydroxy-3-(2-propylphenoxy)propoxy]-4-oxochromene-2-carboxylic acid Chemical compound CCCC1=CC=CC=C1OCC(O)COC1=CC=C(OC(=CC2=O)C(O)=O)C2=C1 KKQCOMIWROCVST-UHFFFAOYSA-N 0.000 description 1
- UYJPUBBNXVJIGE-UHFFFAOYSA-N 7-[2-hydroxy-3-(2-propylphenoxy)propoxy]-4-oxo-6-propylchromene-2-carboxylic acid Chemical compound CCCC1=CC=CC=C1OCC(O)COC(C(=C1)CCC)=CC2=C1C(=O)C=C(C(O)=O)O2 UYJPUBBNXVJIGE-UHFFFAOYSA-N 0.000 description 1
- FZWITJXPWLXCCZ-UHFFFAOYSA-N 7-[2-hydroxy-3-(2-propylphenoxy)propoxy]-4-oxochromene-2-carboxylic acid Chemical compound CCCC1=CC=CC=C1OCC(O)COC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 FZWITJXPWLXCCZ-UHFFFAOYSA-N 0.000 description 1
- SCVJXLLCLNYPBI-UHFFFAOYSA-N 7-[2-hydroxy-3-(4-oxochromen-7-yl)oxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C=2C1=CC(OCC(COC=1C=C3C(C(C=CO3)=O)=CC=1)O)=CC=2 SCVJXLLCLNYPBI-UHFFFAOYSA-N 0.000 description 1
- PPGIDASWJVOWNS-UHFFFAOYSA-N 7-[3-(2,4-ditert-butylphenoxy)-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OCC(O)COC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 PPGIDASWJVOWNS-UHFFFAOYSA-N 0.000 description 1
- IVCLHWVBHNXMSB-UHFFFAOYSA-N 7-[3-(2-tert-butylphenoxy)-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound CC(C)(C)C1=CC=CC=C1OCC(O)COC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 IVCLHWVBHNXMSB-UHFFFAOYSA-N 0.000 description 1
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- LMQBMWHHGVZWMR-UHFFFAOYSA-N 7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropoxy]-4-oxo-8-propyl-1-benzopyran-2-carboxylic acid Chemical compound C1=CC(C(C)=O)=C(O)C(CCC)=C1OCC(O)COC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1CCC LMQBMWHHGVZWMR-UHFFFAOYSA-N 0.000 description 1
- CRKRSRJODGCUCD-UHFFFAOYSA-N 7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound C1=CC(C(C)=O)=C(O)C(CCC)=C1OCC(O)COC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 CRKRSRJODGCUCD-UHFFFAOYSA-N 0.000 description 1
- KIYSCJAMUHJTLU-UHFFFAOYSA-N 7-[3-(4-acetyl-3-hydroxyphenoxy)-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound C1=C(O)C(C(=O)C)=CC=C1OCC(O)COC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 KIYSCJAMUHJTLU-UHFFFAOYSA-N 0.000 description 1
- LLFFWDUMDNUWHQ-UHFFFAOYSA-N 7-[5-(2-tert-butylphenoxy)pentoxy]-4-oxochromene-2-carboxylic acid Chemical compound CC(C)(C)C1=CC=CC=C1OCCCCCOC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 LLFFWDUMDNUWHQ-UHFFFAOYSA-N 0.000 description 1
- HGEDAMWZUWJZQL-UHFFFAOYSA-N 7-[5-(3-methoxyphenoxy)pentoxy]-4-oxochromene-2-carboxylic acid Chemical compound COC1=CC=CC(OCCCCCOC=2C=C3C(C(C=C(O3)C(O)=O)=O)=CC=2)=C1 HGEDAMWZUWJZQL-UHFFFAOYSA-N 0.000 description 1
- COVHOCRZXWWJGI-UHFFFAOYSA-N 7-[5-(4-acetyl-3-hydroxyphenoxy)pentoxy]-4-oxochromene-2-carboxylic acid Chemical compound C1=C(O)C(C(=O)C)=CC=C1OCCCCCOC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 COVHOCRZXWWJGI-UHFFFAOYSA-N 0.000 description 1
- ZUPCVVIVKLPECQ-UHFFFAOYSA-N 7-[5-(4-acetylphenoxy)pentoxy]-4-oxochromene-2-carboxylic acid Chemical compound C1=CC(C(=O)C)=CC=C1OCCCCCOC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 ZUPCVVIVKLPECQ-UHFFFAOYSA-N 0.000 description 1
- WPZVUMPWHLZVKZ-UHFFFAOYSA-N 8-[2-hydroxy-3-(2-iodophenoxy)propoxy]-4-oxochromene-2-carboxylic acid Chemical compound C=1C=CC(C(C=C(O2)C(O)=O)=O)=C2C=1OCC(O)COC1=CC=CC=C1I WPZVUMPWHLZVKZ-UHFFFAOYSA-N 0.000 description 1
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- OLHWLZPQZNPXNF-UHFFFAOYSA-N 8-[3-(2-butylphenoxy)-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound CCCCC1=CC=CC=C1OCC(O)COC1=CC=CC2=C1OC(C(O)=O)=CC2=O OLHWLZPQZNPXNF-UHFFFAOYSA-N 0.000 description 1
- CLZNORDRONIRDL-UHFFFAOYSA-N 8-[3-(2-butylphenoxy)propoxy]-4-oxochromene-2-carboxylic acid Chemical compound CCCCC1=CC=CC=C1OCCCOC1=CC=CC2=C1OC(C(O)=O)=CC2=O CLZNORDRONIRDL-UHFFFAOYSA-N 0.000 description 1
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
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- JPKKQJKQTPNWTR-KQAYXBCTSA-N [(1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2r)-3-hydroxy-2-phenylpropanoate;sulfuric acid;hydrate Chemical compound O.OS(O)(=O)=O.C1([C@H](CO)C(=O)OC2C[C@H]3CC[C@@H](C2)N3C)=CC=CC=C1.C1([C@H](CO)C(=O)OC2C[C@H]3CC[C@@H](C2)N3C)=CC=CC=C1 JPKKQJKQTPNWTR-KQAYXBCTSA-N 0.000 description 1
- HOBWAPHTEJGALG-JKCMADFCSA-N [(1r,5s)-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;sulfate Chemical compound [O-]S([O-])(=O)=O.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1 HOBWAPHTEJGALG-JKCMADFCSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000004479 aerosol dispenser Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
- 229960002028 atropine sulfate Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
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- 201000010099 disease Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 231100000255 pathogenic effect Toxicity 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 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 in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3061/77A GB1583691A (en) | 1977-01-26 | 1977-01-26 | Benzopyrans |
| GB4133077 | 1977-10-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH627463A5 true CH627463A5 (en) | 1982-01-15 |
Family
ID=26237992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH80978A CH627463A5 (en) | 1977-01-26 | 1978-01-25 | Salts of basic amino sugars or of basic amino acids |
Country Status (15)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5829773A (ja) * | 1981-08-06 | 1983-02-22 | ビ−チヤム・グル−プ・ピ−エルシ− | 医薬活性化合物、その製法及びそれを含む医薬組成物 |
| KR100320588B1 (ko) * | 1999-04-28 | 2002-01-12 | 손화섭 | 개 정액 냉동용 조성물, 이를 이용한 개 정액 냉동방법 및이 냉동된 정액을 이용한 인공수정 방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1384530A (en) * | 1971-07-29 | 1975-02-19 | Fisons Ltd | Chromone derivatives |
-
1978
- 1978-01-23 SE SE7800809A patent/SE7800809L/xx unknown
- 1978-01-23 FI FI780195A patent/FI780195A7/fi not_active Application Discontinuation
- 1978-01-24 NZ NZ186298A patent/NZ186298A/xx unknown
- 1978-01-24 DK DK34378A patent/DK34378A/da not_active Application Discontinuation
- 1978-01-24 NL NL7800818A patent/NL7800818A/xx not_active Application Discontinuation
- 1978-01-24 AU AU32694/78A patent/AU513311B2/en not_active Expired
- 1978-01-24 IL IL53873A patent/IL53873A0/xx unknown
- 1978-01-25 CH CH80978A patent/CH627463A5/fr not_active IP Right Cessation
- 1978-01-25 DE DE19782803230 patent/DE2803230A1/de not_active Withdrawn
- 1978-01-25 NO NO780267A patent/NO780267L/no unknown
- 1978-01-25 IE IE164/78A patent/IE46382B1/en unknown
- 1978-01-25 LU LU78943A patent/LU78943A1/xx unknown
- 1978-01-25 ES ES78466305A patent/ES466305A1/es not_active Expired
- 1978-01-25 FR FR7802033A patent/FR2378795A1/fr active Granted
- 1978-01-26 JP JP677778A patent/JPS5392775A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7800818A (nl) | 1978-07-28 |
| FR2378795A1 (fr) | 1978-08-25 |
| LU78943A1 (fr) | 1978-09-28 |
| SE7800809L (sv) | 1978-07-27 |
| NZ186298A (en) | 1979-10-25 |
| IL53873A0 (en) | 1978-04-30 |
| JPS5392775A (en) | 1978-08-15 |
| FR2378795B1 (enrdf_load_stackoverflow) | 1980-04-25 |
| AU513311B2 (en) | 1980-11-27 |
| IE780164L (en) | 1978-07-26 |
| FI780195A7 (fi) | 1978-07-27 |
| DE2803230A1 (de) | 1978-07-27 |
| ES466305A1 (es) | 1978-10-01 |
| AU3269478A (en) | 1979-08-02 |
| IE46382B1 (en) | 1983-05-18 |
| NO780267L (no) | 1978-07-27 |
| DK34378A (da) | 1978-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |