IE41904B1 - Substituted 3-(1-aminoethylidene)-5-cinnamoyl-2h-pyran-2,6(3h)-diones - Google Patents

Substituted 3-(1-aminoethylidene)-5-cinnamoyl-2h-pyran-2,6(3h)-diones

Info

Publication number: IE41904B1
Authority: IE; Ireland
Prior art keywords: compound according; formula; chemical; hydroxy; pyran
Prior art date: 1974-10-02

Application number

IE2125/75A

Other languages

English (en)

Other versions

IE41904L (en

Original Assignee

Smithkline Corp

Priority date (The priority date 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 date listed.)

1974-10-02

Filing date

1975-09-29

Publication date

1980-04-23

1975-09-29 Application filed by Smithkline Corp filed Critical Smithkline Corp

1976-04-02 Publication of IE41904L publication Critical patent/IE41904L/xx

1980-04-23 Publication of IE41904B1 publication Critical patent/IE41904B1/en

Links

BIQSMAFLRVMGRO-UHFFFAOYSA-N 3-(1-aminoethylidene)-5-(3-phenylprop-2-enoyl)pyran-2,6-dione Chemical class O=C1OC(=O)C(=C(N)C)C=C1C(=O)C=CC1=CC=CC=C1 BIQSMAFLRVMGRO-UHFFFAOYSA-N 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 40
-1 methoxyphenyl Chemical group 0.000 claims abstract description 21
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
239000003937 drug carrier Substances 0.000 claims abstract description 4
125000004464 hydroxyphenyl group Chemical group 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
125000005059 halophenyl group Chemical group 0.000 claims abstract description 3
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
239000000126 substance Substances 0.000 claims description 10
238000000034 method Methods 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
OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 claims description 5
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 3
125000004799 bromophenyl group Chemical group 0.000 claims description 2
125000000068 chlorophenyl group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 2
101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims 1
150000001299 aldehydes Chemical class 0.000 claims 1
150000003935 benzaldehydes Chemical class 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 2
238000011282 treatment Methods 0.000 abstract description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 20
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 15
241000700159 Rattus Species 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
208000024780 Urticaria Diseases 0.000 description 9
230000005764 inhibitory process Effects 0.000 description 9
239000007787 solid Substances 0.000 description 9
CZVTYGFISHLVHK-UHFFFAOYSA-N 4h-pyran-2,3-dione Chemical class O=C1CC=COC1=O CZVTYGFISHLVHK-UHFFFAOYSA-N 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 description 6
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000003085 diluting agent Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
238000012360 testing method Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
238000009835 boiling Methods 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 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
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
235000021355 Stearic acid Nutrition 0.000 description 3
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 3
229930006000 Sucrose Natural products 0.000 description 3
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
239000008117 stearic acid Substances 0.000 description 3
239000005720 sucrose Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-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
ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 2
APOUINGVDCMXPJ-UHFFFAOYSA-N 5-acetyl-4,6-dihydroxy-3-[N-(2-hydroxyphenyl)-C-methylcarbonimidoyl]pyran-2-one Chemical compound CC(=NC1=CC=CC=C1O)C2=C(C(=C(OC2=O)O)C(=O)C)O APOUINGVDCMXPJ-UHFFFAOYSA-N 0.000 description 2
206010002198 Anaphylactic reaction Diseases 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
108010010803 Gelatin Proteins 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
229920002472 Starch Polymers 0.000 description 2
230000000172 allergic effect Effects 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
208000010668 atopic eczema 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
238000012866 crystallographic experiment Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
229960003699 evans blue Drugs 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
229960001340 histamine Drugs 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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
239000008024 pharmaceutical diluent Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
229940076279 serotonin Drugs 0.000 description 2
239000002904 solvent Substances 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000003826 tablet Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-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
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
FPSFHENOHWPNPB-UHFFFAOYSA-N 3-(1-anilinoethylidene)-4-hydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]pyran-2,6-dione Chemical compound O=C1OC(=O)C(C(=O)C=CC=2C=CC(O)=CC=2)=C(O)C1=C(C)NC1=CC=CC=C1 FPSFHENOHWPNPB-UHFFFAOYSA-N 0.000 description 1
UZVRVLVUIJYPFH-UHFFFAOYSA-N 3-[1-(2-aminoanilino)ethylidene]-4-hydroxy-5-[3-(3-hydroxyphenyl)prop-2-enoyl]pyran-2,6-dione Chemical compound O=C1OC(=O)C(C(=O)C=CC=2C=C(O)C=CC=2)=C(O)C1=C(C)NC1=CC=CC=C1N UZVRVLVUIJYPFH-UHFFFAOYSA-N 0.000 description 1
QVPLPSILOATTOW-UHFFFAOYSA-N 3-acetyl-5-(1-aminoethylidene)pyran-2,6-dione Chemical compound CC(N)=C1C=C(C(C)=O)C(=O)OC1=O QVPLPSILOATTOW-UHFFFAOYSA-N 0.000 description 1
WCDSVWRUXWCYFN-UHFFFAOYSA-N 4-aminobenzenethiol Chemical compound NC1=CC=C(S)C=C1 WCDSVWRUXWCYFN-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
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 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
102000004506 Blood Proteins Human genes 0.000 description 1
108010017384 Blood Proteins Proteins 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 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
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
239000003708 ampul Substances 0.000 description 1
229940095672 calcium sulfate Drugs 0.000 description 1
PASHVRUKOFIRIK-UHFFFAOYSA-L calcium sulfate dihydrate Chemical compound O.O.[Ca+2].[O-]S([O-])(=O)=O PASHVRUKOFIRIK-UHFFFAOYSA-L 0.000 description 1
230000004856 capillary permeability Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
230000021615 conjugation Effects 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
229940057307 dihydrate calcium sulfate Drugs 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
238000001035 drying 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
238000001914 filtration Methods 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
229940074045 glyceryl distearate Drugs 0.000 description 1
229940075507 glyceryl monostearate Drugs 0.000 description 1
239000008187 granular material Substances 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
239000003112 inhibitor Substances 0.000 description 1
230000003993 interaction Effects 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
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
229910052757 nitrogen Inorganic materials 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 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
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
238000010626 work up procedure Methods 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
- C07D309/38—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 one oxygen atom in position 2 or 4, e.g. pyrones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pulmonology (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IE2125/75A 1974-10-02 1975-09-29 Substituted 3-(1-aminoethylidene)-5-cinnamoyl-2h-pyran-2,6(3h)-diones IE41904B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US51115274A	1974-10-02	1974-10-02

Publications (2)

Publication Number	Publication Date
IE41904L IE41904L (en)	1976-04-02
IE41904B1 true IE41904B1 (en)	1980-04-23

Family

ID=24033663

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE2125/75A IE41904B1 (en)	1974-10-02	1975-09-29	Substituted 3-(1-aminoethylidene)-5-cinnamoyl-2h-pyran-2,6(3h)-diones

Country Status (8)

Country	Link
JP (1)	JPS6039674B2 (fr)
BE (1)	BE834082A (fr)
CA (1)	CA1064510A (fr)
DE (1)	DE2544130C2 (fr)
FR (1)	FR2324296A1 (fr)
GB (1)	GB1527375A (fr)
IE (1)	IE41904B1 (fr)
ZA (1)	ZA756230B (fr)

1975
- 1975-09-11 GB GB37417/75A patent/GB1527375A/en not_active Expired
- 1975-09-29 JP JP50118228A patent/JPS6039674B2/ja not_active Expired
- 1975-09-29 IE IE2125/75A patent/IE41904B1/en unknown
- 1975-10-01 CA CA236,818A patent/CA1064510A/fr not_active Expired
- 1975-10-01 BE BE160598A patent/BE834082A/fr not_active IP Right Cessation
- 1975-10-01 ZA ZA00756230A patent/ZA756230B/xx unknown
- 1975-10-01 FR FR7530087A patent/FR2324296A1/fr active Granted
- 1975-10-02 DE DE2544130A patent/DE2544130C2/de not_active Expired

Also Published As

Publication number	Publication date
JPS6039674B2 (ja)	1985-09-06
FR2324296B1 (fr)	1978-09-01
CA1064510A (fr)	1979-10-16
DE2544130C2 (de)	1985-05-15
FR2324296A1 (fr)	1977-04-15
GB1527375A (en)	1978-10-04
BE834082A (fr)	1976-04-01
ZA756230B (en)	1976-09-29
IE41904L (en)	1976-04-02
JPS5159868A (fr)	1976-05-25
AU8537975A (en)	1977-04-07
DE2544130A1 (de)	1976-04-15

Publication	Publication Date	Title
US3946022A (en)	1976-03-23	Piperidine derivatives
US3931197A (en)	1976-01-06	Substituted piperidine derivatives
EP0167901A2 (fr)	1986-01-15	Composés actifs
US3975380A (en)	1976-08-17	Substituted aurones
US3459767A (en)	1969-08-05	Aminomethylindoles
GB1568398A (en)	1980-05-29	Triazolo pyridazine derivatives
US4017633A (en)	1977-04-12	Substituted 3-(1-aminoethylidene)-5-cinnamoyl-2H-pyran-2,6(3H)-diones
US4032652A (en)	1977-06-28	Substituted 2h-pyran-2,6(3h)-dione derivatives, pharmaceutical compositions comprising such derivatives and methods of inhibiting the antigen-antibody reaction
US3530126A (en)	1970-09-22	N-heterocyclic substituted cyclohexanes
US4015009A (en)	1977-03-29	Pharmaceutical compositions comprising substituted 3-cinnamoyl-2H-pyran-2,6(3H)-diones
IE41904B1 (en)	1980-04-23	Substituted 3-(1-aminoethylidene)-5-cinnamoyl-2h-pyran-2,6(3h)-diones
US4025642A (en)	1977-05-24	Substituted 2H-pyran-2, 6(3H)-dione derivatives
US4025614A (en)	1977-05-24	Substituted 2H-pyran-2,6 (3H)-dione derivatives useful in treatment of allergic reactions
US3929812A (en)	1975-12-30	Derivatives of 1H-triazolo {8 4,5-c{9 pyridine-7-carboxylic acids and esters
IE41709B1 (en)	1980-03-12	5-acetyl-4-hydroxy-2h-pyran-2,6(3h)-dione derivatives and pharmaceutical compositions comprising such compounds
US4117226A (en)	1978-09-26	Substituted 3-cinnamoyl-2h-pyran-2,6(3h)-diones
US3978044A (en)	1976-08-31	Indazole derivatives, processes for making the same and pharmaceutical compositions
US4127646A (en)	1978-11-28	Substituted 2H-pyran-2,6(3H)-dione derivatives
US4122201A (en)	1978-10-24	Method of treating asthma with 4,6-dihydroxy-2H-pyran-2-ones
US4165365A (en)	1979-08-21	Substituted 2H-pyran-2,6(3H)-dione derivatives
US4160021A (en)	1979-07-03	Substituted 2H-pyran-2,6(3H)-dione derivatives
US3452011A (en)	1969-06-24	4-phenyl-perhydrocycloalkoxazines
US3542927A (en)	1970-11-24	Reduction of blood sugar levels with aminomethylindoles
US4153720A (en)	1979-05-08	3-Acyl-5-alkyl-2H-pyran-2,4,6-(3H,5H)-triones and their 4-hydroxy tautomers
JPH0227356B2 (fr)	1990-06-15