IE41905B1 - Pharmaceutical compositions comprising substituted 3-cinnamoyl-2h-pyran-2,6(3h)-diones - Google Patents
Pharmaceutical compositions comprising substituted 3-cinnamoyl-2h-pyran-2,6(3h)-dionesInfo
- Publication number
- IE41905B1 IE41905B1 IE2126/75A IE212675A IE41905B1 IE 41905 B1 IE41905 B1 IE 41905B1 IE 2126/75 A IE2126/75 A IE 2126/75A IE 212675 A IE212675 A IE 212675A IE 41905 B1 IE41905 B1 IE 41905B1
- Authority
- IE
- Ireland
- Prior art keywords
- hydroxy
- acetamido
- pharmaceutical composition
- formula
- composition according
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 18
- NKPVIJNMEQRGPN-UHFFFAOYSA-N 3-(3-phenylprop-2-enoyl)-3h-pyran-2,6-dione Chemical class C1=CC(=O)OC(=O)C1C(=O)C=CC1=CC=CC=C1 NKPVIJNMEQRGPN-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- -1 methoxy, hydroxy, carboxy-methyleneoxy, acetamido Chemical group 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 23
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 9
- ISDVKWGLGFGXJD-UHFFFAOYSA-N chembl3248291 Chemical compound CC(=O)C1=C(O)OC(=O)C(C(C)=O)=C1O ISDVKWGLGFGXJD-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000008223 sterile water Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- JLWVYWHENWCOFH-UHFFFAOYSA-N C(C)(=O)C=1C(OCC(C=1O)(O)C(C)=O)=O Chemical compound C(C)(=O)C=1C(OCC(C=1O)(O)C(C)=O)=O JLWVYWHENWCOFH-UHFFFAOYSA-N 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 150000003935 benzaldehydes Chemical class 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 239000001117 sulphuric acid Substances 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 abstract description 2
- 238000011282 treatment Methods 0.000 abstract description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 241000700159 Rattus Species 0.000 description 9
- 208000024780 Urticaria Diseases 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 description 4
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000000427 antigen Substances 0.000 description 4
- 102000036639 antigens Human genes 0.000 description 4
- 108091007433 antigens Proteins 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- SYIUWAVTBADRJG-UHFFFAOYSA-N 2H-pyran-2,6(3H)-dione Chemical compound O=C1CC=CC(=O)O1 SYIUWAVTBADRJG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000008024 pharmaceutical diluent Substances 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
- VHBHWQCXLFIMJR-UHFFFAOYSA-N 4,6-dihydroxypyran-2-one Chemical compound OC=1C=C(O)OC(=O)C=1 VHBHWQCXLFIMJR-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- ZVTPLASNCIDWSK-UHFFFAOYSA-N 5-acetyl-2-methyl-4,6-dioxopyran-3-carboxylic acid Chemical compound CC(=O)C1C(=O)OC(C)=C(C(O)=O)C1=O ZVTPLASNCIDWSK-UHFFFAOYSA-N 0.000 description 2
- MPMAPZBJCRCZNY-UHFFFAOYSA-N 5-acetyl-4-hydroxy-3-[3-(4-hydroxyphenyl)prop-2-enoyl]-3h-pyran-2,6-dione Chemical compound O=C1OC(=O)C(C(=O)C)=C(O)C1C(=O)C=CC1=CC=C(O)C=C1 MPMAPZBJCRCZNY-UHFFFAOYSA-N 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 2
- 241000359025 Equus kiang Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 108010058846 Ovalbumin Proteins 0.000 description 2
- 241001167578 Phyllomys brasiliensis Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229960003699 evans blue Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229960001340 histamine Drugs 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
- 238000002156 mixing Methods 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- 239000006199 nebulizer Substances 0.000 description 2
- 229940092253 ovalbumin Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 2
- AFUKNJHPZAVHGQ-UHFFFAOYSA-N 2,5-dimethoxy-Benzaldehyde Chemical compound COC1=CC=C(OC)C(C=O)=C1 AFUKNJHPZAVHGQ-UHFFFAOYSA-N 0.000 description 1
- OYNIIKHNXNPSAG-UHFFFAOYSA-N 2-(4-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C=O)C=C1 OYNIIKHNXNPSAG-UHFFFAOYSA-N 0.000 description 1
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- GSSXLFACIJSBOM-UHFFFAOYSA-N 2h-pyran-2-ol Chemical compound OC1OC=CC=C1 GSSXLFACIJSBOM-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- JHUXTYBBBLZQER-UHFFFAOYSA-N 5-acetyl-3-[3-(2,3-dimethoxyphenyl)prop-2-enoyl]-4-hydroxy-3h-pyran-2,6-dione Chemical compound COC1=CC=CC(C=CC(=O)C2C(=C(C(C)=O)C(=O)OC2=O)O)=C1OC JHUXTYBBBLZQER-UHFFFAOYSA-N 0.000 description 1
- NVGIGMSSSCNZLC-UHFFFAOYSA-N 5-acetyl-3-[3-(2,5-dimethoxyphenyl)prop-2-enoyl]-4-hydroxy-3h-pyran-2,6-dione Chemical compound COC1=CC=C(OC)C(C=CC(=O)C2C(=C(C(C)=O)C(=O)OC2=O)O)=C1 NVGIGMSSSCNZLC-UHFFFAOYSA-N 0.000 description 1
- ABSQJKMWIHFCRN-UHFFFAOYSA-N 5-acetyl-4-hydroxy-3-(3-phenylprop-2-enoyl)-3h-pyran-2,6-dione Chemical compound O=C1OC(=O)C(C(=O)C)=C(O)C1C(=O)C=CC1=CC=CC=C1 ABSQJKMWIHFCRN-UHFFFAOYSA-N 0.000 description 1
- LHGAPRYJBFROQX-UHFFFAOYSA-N 5-acetyl-4-hydroxy-3-[3-(3-hydroxyphenyl)prop-2-enoyl]-3h-pyran-2,6-dione Chemical compound O=C1OC(=O)C(C(=O)C)=C(O)C1C(=O)C=CC1=CC=CC(O)=C1 LHGAPRYJBFROQX-UHFFFAOYSA-N 0.000 description 1
- JDYUSMPXDGJFEN-UHFFFAOYSA-N 5-acetyl-4-hydroxy-3-[3-(4-methylphenyl)prop-2-enoyl]-3h-pyran-2,6-dione Chemical compound O=C1OC(=O)C(C(=O)C)=C(O)C1C(=O)C=CC1=CC=C(C)C=C1 JDYUSMPXDGJFEN-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 208000000884 Airway Obstruction Diseases 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- XEJAAABYQGEPOO-UHFFFAOYSA-N C(C)(=O)C=1COC(=C(C1O)C(C)=O)O Chemical compound C(C)(=O)C=1COC(=C(C1O)C(C)=O)O XEJAAABYQGEPOO-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 201000005702 Pertussis Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- KBKWZUVMKBNTFP-UHFFFAOYSA-N n-(3-formylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C=O)=C1 KBKWZUVMKBNTFP-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51115374A | 1974-10-02 | 1974-10-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41905L IE41905L (en) | 1976-04-02 |
| IE41905B1 true IE41905B1 (en) | 1980-04-23 |
Family
ID=24033666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2126/75A IE41905B1 (en) | 1974-10-02 | 1975-09-29 | Pharmaceutical compositions comprising substituted 3-cinnamoyl-2h-pyran-2,6(3h)-diones |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5159869A (cg-RX-API-DMAC10.html) |
| BE (1) | BE834081A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1076591A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2544131C2 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2286647A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1527236A (cg-RX-API-DMAC10.html) |
| IE (1) | IE41905B1 (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA756231B (cg-RX-API-DMAC10.html) |
-
1975
- 1975-09-11 GB GB37418/75A patent/GB1527236A/en not_active Expired
- 1975-09-29 IE IE2126/75A patent/IE41905B1/en unknown
- 1975-09-29 JP JP50118229A patent/JPS5159869A/ja active Pending
- 1975-10-01 ZA ZA00756231A patent/ZA756231B/xx unknown
- 1975-10-01 BE BE160597A patent/BE834081A/xx not_active IP Right Cessation
- 1975-10-01 CA CA236,817A patent/CA1076591A/en not_active Expired
- 1975-10-02 DE DE2544131A patent/DE2544131C2/de not_active Expired
- 1975-10-02 FR FR7530206A patent/FR2286647A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2544131A1 (de) | 1976-04-15 |
| FR2286647B1 (cg-RX-API-DMAC10.html) | 1979-09-14 |
| JPS5159869A (cg-RX-API-DMAC10.html) | 1976-05-25 |
| IE41905L (en) | 1976-04-02 |
| GB1527236A (en) | 1978-10-04 |
| BE834081A (fr) | 1976-04-01 |
| ZA756231B (en) | 1976-09-29 |
| CA1076591A (en) | 1980-04-29 |
| FR2286647A1 (fr) | 1976-04-30 |
| AU8538075A (en) | 1977-04-07 |
| DE2544131C2 (de) | 1984-04-19 |
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