NO780267L - Fremgangsmaate til fremstilling av et salt med et basisk aminosukker eller en basisk aminosyre av benzopyranderivater - Google Patents
Fremgangsmaate til fremstilling av et salt med et basisk aminosukker eller en basisk aminosyre av benzopyranderivaterInfo
- Publication number
- NO780267L NO780267L NO780267A NO780267A NO780267L NO 780267 L NO780267 L NO 780267L NO 780267 A NO780267 A NO 780267A NO 780267 A NO780267 A NO 780267A NO 780267 L NO780267 L NO 780267L
- Authority
- NO
- Norway
- Prior art keywords
- basic amino
- hydroxy
- benzopyran
- oxo
- carboxylic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 150000002337 glycosamines Chemical class 0.000 title claims description 14
- 150000001413 amino acids Chemical class 0.000 title claims description 13
- 150000003839 salts Chemical class 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000001562 benzopyrans Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 36
- -1 amino, amino Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000012153 distilled water Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000004108 freeze drying Methods 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 239000004475 Arginine Substances 0.000 claims description 4
- 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
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 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
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 229960003104 ornithine Drugs 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000011146 sterile filtration Methods 0.000 claims description 4
- 239000000725 suspension Substances 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
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 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
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229960002442 glucosamine Drugs 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 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 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical group CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000002947 alkylene 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
- 239000000706 filtrate Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 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
- 239000000126 substance Substances 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 16
- 235000001014 amino acid Nutrition 0.000 description 10
- 230000000694 effects Effects 0.000 description 5
- 210000003405 ileum Anatomy 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 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 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229960002028 atropine sulfate Drugs 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003536 tetrazoles Chemical group 0.000 description 2
- BIQYAKGJUUYTCQ-UHFFFAOYSA-N 4-oxo-6-propyl-7-[3-(2-propylphenoxy)propoxy]chromene-2-carboxylic acid Chemical compound CCCC1=CC=CC=C1OCCCOC(C(=C1)CCC)=CC2=C1C(=O)C=C(C(O)=O)O2 BIQYAKGJUUYTCQ-UHFFFAOYSA-N 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
- 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
- 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
- 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 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
- 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 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
- FERILSOAIWBKNA-UHFFFAOYSA-N 8-[2-hydroxy-3-(2-propylphenoxy)propoxy]-4-oxochromene-2-carboxylic acid Chemical compound CCCC1=CC=CC=C1OCC(O)COC1=CC=CC2=C1OC(C(O)=O)=CC2=O FERILSOAIWBKNA-UHFFFAOYSA-N 0.000 description 1
- 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
- WAGAAZRIEXUFHI-UHFFFAOYSA-N 8-[3-(2-tert-butylphenoxy)-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound CC(C)(C)C1=CC=CC=C1OCC(O)COC1=CC=CC2=C1OC(C(O)=O)=CC2=O WAGAAZRIEXUFHI-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 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
- 235000019766 L-Lysine Nutrition 0.000 description 1
- 150000008545 L-lysines Chemical class 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008121 dextrose Substances 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
- 239000004744 fabric Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000018977 lysine Nutrition 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
- 239000000203 mixture Substances 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
- 230000001575 pathological effect Effects 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- 230000003252 repetitive effect 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
- 239000007787 solid Substances 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 239000007858 starting material Substances 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
- 238000005406 washing Methods 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 |
|---|---|
| NO780267L true NO780267L (no) | 1978-07-27 |
Family
ID=26237992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO780267A NO780267L (no) | 1977-01-26 | 1978-01-25 | Fremgangsmaate til fremstilling av et salt med et basisk aminosukker eller en basisk aminosyre av benzopyranderivater |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5392775A (cg-RX-API-DMAC10.html) |
| AU (1) | AU513311B2 (cg-RX-API-DMAC10.html) |
| CH (1) | CH627463A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2803230A1 (cg-RX-API-DMAC10.html) |
| DK (1) | DK34378A (cg-RX-API-DMAC10.html) |
| ES (1) | ES466305A1 (cg-RX-API-DMAC10.html) |
| FI (1) | FI780195A7 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2378795A1 (cg-RX-API-DMAC10.html) |
| IE (1) | IE46382B1 (cg-RX-API-DMAC10.html) |
| IL (1) | IL53873A0 (cg-RX-API-DMAC10.html) |
| LU (1) | LU78943A1 (cg-RX-API-DMAC10.html) |
| NL (1) | NL7800818A (cg-RX-API-DMAC10.html) |
| NO (1) | NO780267L (cg-RX-API-DMAC10.html) |
| NZ (1) | NZ186298A (cg-RX-API-DMAC10.html) |
| SE (1) | SE7800809L (cg-RX-API-DMAC10.html) |
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 FI FI780195A patent/FI780195A7/fi not_active Application Discontinuation
- 1978-01-23 SE SE7800809A patent/SE7800809L/xx unknown
- 1978-01-24 DK DK34378A patent/DK34378A/da not_active Application Discontinuation
- 1978-01-24 IL IL53873A patent/IL53873A0/xx unknown
- 1978-01-24 NZ NZ186298A patent/NZ186298A/xx unknown
- 1978-01-24 AU AU32694/78A patent/AU513311B2/en not_active Expired
- 1978-01-24 NL NL7800818A patent/NL7800818A/xx not_active Application Discontinuation
- 1978-01-25 CH CH80978A patent/CH627463A5/fr not_active IP Right Cessation
- 1978-01-25 FR FR7802033A patent/FR2378795A1/fr active Granted
- 1978-01-25 LU LU78943A patent/LU78943A1/xx unknown
- 1978-01-25 DE DE19782803230 patent/DE2803230A1/de not_active Withdrawn
- 1978-01-25 IE IE164/78A patent/IE46382B1/en unknown
- 1978-01-25 ES ES78466305A patent/ES466305A1/es not_active Expired
- 1978-01-25 NO NO780267A patent/NO780267L/no unknown
- 1978-01-26 JP JP677778A patent/JPS5392775A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5392775A (en) | 1978-08-15 |
| LU78943A1 (fr) | 1978-09-28 |
| DK34378A (da) | 1978-07-27 |
| DE2803230A1 (de) | 1978-07-27 |
| IL53873A0 (en) | 1978-04-30 |
| FR2378795B1 (cg-RX-API-DMAC10.html) | 1980-04-25 |
| NZ186298A (en) | 1979-10-25 |
| ES466305A1 (es) | 1978-10-01 |
| FI780195A7 (fi) | 1978-07-27 |
| IE780164L (en) | 1978-07-26 |
| FR2378795A1 (fr) | 1978-08-25 |
| AU513311B2 (en) | 1980-11-27 |
| IE46382B1 (en) | 1983-05-18 |
| AU3269478A (en) | 1979-08-02 |
| CH627463A5 (en) | 1982-01-15 |
| NL7800818A (nl) | 1978-07-28 |
| SE7800809L (sv) | 1978-07-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR0178544B1 (ko) | 안과용 순수 히알우론산 분류물 및 그의 정제방법 | |
| KR100844918B1 (ko) | 알긴올리고당 및 그 유도체 및 그 제조방법과 용도 | |
| JPS5953883B2 (ja) | 「はん」痕形成剤 | |
| DK153948B (da) | Analogifremgangsmaade til fremstilling af vandoploeselige associationsprodukter af (+)-katekin med en aminosyre og eventuelt tillige en anden syre | |
| KR20150035491A (ko) | Hsya 나트륨염, 그의 제조방법 및 그의 용도 | |
| FI84065C (fi) | Foerfarande foer framstaellning av isosilybinfri silibinin. | |
| DK160317B (da) | Fremgangsmaade til fremstilling af et injicerbart chondroitinpolysulfat | |
| WO1990008135A1 (fr) | Monohydrate d'hydrochlorure d'acide ethyle ester 6-brome-5-hydroxy-4-dimethyle-aminomethyle-1-methyle-2-phenylthiomethyle indole-3-carboxylique, son procede d'obtention et preparation pharmaceutique presentant une activite antivirale, de stimulation d'interferon et d'immunomodulation basee sur ledit compose | |
| DK154768B (da) | Analogifremgangsmaade til fremstilling af estere af 9-hydroxyalkylhypoxanthiner eller farmaceutisk acceptable salte heraf | |
| US4213903A (en) | Basic amino acid salts of chromones | |
| DE3152621C2 (cg-RX-API-DMAC10.html) | ||
| NO780267L (no) | Fremgangsmaate til fremstilling av et salt med et basisk aminosukker eller en basisk aminosyre av benzopyranderivater | |
| CA1166643A (en) | Salt of ¬(1-benzyl-1h-indazol-3-yl)oxy| acetic acid (or bendazac) with the lysine | |
| JPH07223940A (ja) | 活性酸素消去剤及びこれを含有する組成物 | |
| DK164865B (da) | Silibininderivater, fremgangsmaade til fremstilling deraf samt farmaceutisk middel indeholdende silibininderivaterne | |
| EP0069380A1 (en) | 11-Deoxoglycyrrhetinic acid hydrogen maleate, process for its production, and its use as a medicine | |
| CN106928063A (zh) | 巨大戟二萜醇类化合物及其在抗hiv潜伏治疗上的应用 | |
| JPWO1997022628A1 (ja) | 血管内膜肥厚抑制剤 | |
| Shimizu | Pharmacological and chemical studies on" senso," the dried venom of the Chinese toad | |
| DE69300945T2 (de) | Fettstoffwechsel verbessernde Zusammensetzung. | |
| EP0640074B1 (en) | Salts of a quinolone-carboxylic acid | |
| EP0198878A1 (fr) | Application du diethyldithiocarbamate (dtc) a la preparation d'un medicament et son procede de preparation. | |
| JPH069634A (ja) | 血液循環中断後の筋損傷の治療のためのキサンチン誘導体の使用 | |
| JPH05112463A (ja) | 白内障治療剤 | |
| JPH11130672A (ja) | 脂質過酸化抑制剤 |