CA1064509A - Substituted 2h-pyran-2,6(3h)-dione derivatives - Google Patents
Substituted 2h-pyran-2,6(3h)-dione derivativesInfo
- Publication number
- CA1064509A CA1064509A CA231,964A CA231964A CA1064509A CA 1064509 A CA1064509 A CA 1064509A CA 231964 A CA231964 A CA 231964A CA 1064509 A CA1064509 A CA 1064509A
- Authority
- CA
- Canada
- Prior art keywords
- pyran
- dione
- acetyl
- hydroxy
- ethylidene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- SYIUWAVTBADRJG-UHFFFAOYSA-N 2H-pyran-2,6(3H)-dione Chemical class O=C1CC=CC(=O)O1 SYIUWAVTBADRJG-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 10
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- -1 N,N-dimethylcarbamoyloxyphenyl Chemical group 0.000 claims description 28
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 6
- AQLRBSWLNBCSJD-UHFFFAOYSA-N 5-acetyl-4,6-dihydroxy-3-[N-(4-hydroxyphenyl)-C-methylcarbonimidoyl]pyran-2-one Chemical compound CC(=NC1=CC=C(C=C1)O)C2=C(C(=C(OC2=O)O)C(=O)C)O AQLRBSWLNBCSJD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 26
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 12
- 239000004480 active ingredient Substances 0.000 abstract description 6
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 abstract description 5
- 239000008194 pharmaceutical composition Chemical class 0.000 abstract description 4
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 208000024780 Urticaria Diseases 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical class C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
- 229940076134 benzene Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 150000002500 ions Chemical class 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
- 241000359025 Equus kiang Species 0.000 description 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 229940086542 triethylamine Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 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 2
- 230000000172 allergic effect Effects 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 208000003455 anaphylaxis 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
- 229940079593 drug Drugs 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 210000004072 lung Anatomy 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
- 239000000463 material Substances 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
- 230000003595 spectral effect Effects 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- WWYNJERNGUHSAO-XUDSTZEESA-N (+)-Norgestrel Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 WWYNJERNGUHSAO-XUDSTZEESA-N 0.000 description 1
- VRXLPSVAKDQLPT-UHFFFAOYSA-N (4-aminophenyl) carbamate;hydrochloride Chemical compound Cl.NC(=O)OC1=CC=C(N)C=C1 VRXLPSVAKDQLPT-UHFFFAOYSA-N 0.000 description 1
- XVCKCCODMHCXJD-UHFFFAOYSA-N (4-aminophenyl)urea Chemical compound NC(=O)NC1=CC=C(N)C=C1 XVCKCCODMHCXJD-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- UQRKJSTUONFWFR-UHFFFAOYSA-N 3-acetyl-4-hydroxy-5-[1-(3-hydroxyanilino)ethylidene]pyran-2,6-dione Chemical compound O=C1OC(=O)C(C(=O)C)=C(O)C1=C(C)NC1=CC=CC(O)=C1 UQRKJSTUONFWFR-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- VHBHWQCXLFIMJR-UHFFFAOYSA-N 4,6-dihydroxypyran-2-one Chemical compound OC=1C=C(O)OC(=O)C=1 VHBHWQCXLFIMJR-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
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-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
- BQSKTEVABWFVAI-UHFFFAOYSA-N 5-acetyl-3-[N-(2-aminophenyl)-C-methylcarbonimidoyl]-4,6-dihydroxypyran-2-one Chemical compound CC(=NC1=CC=CC=C1N)C2=C(C(=C(OC2=O)O)C(=O)C)O BQSKTEVABWFVAI-UHFFFAOYSA-N 0.000 description 1
- VVFOFYBPWXZICQ-UHFFFAOYSA-N 5-acetyl-3-[N-(4-fluorophenyl)-C-methylcarbonimidoyl]-4,6-dihydroxypyran-2-one Chemical compound CC(=NC1=CC=C(C=C1)F)C2=C(C(=C(OC2=O)O)C(=O)C)O VVFOFYBPWXZICQ-UHFFFAOYSA-N 0.000 description 1
- KJPJNOOJLYNTID-UHFFFAOYSA-N 5-acetyl-4,6-dihydroxy-3-[C-methyl-N-(4-sulfanylphenyl)carbonimidoyl]pyran-2-one Chemical compound CC(=NC1=CC=C(C=C1)S)C2=C(C(=C(OC2=O)O)C(=O)C)O KJPJNOOJLYNTID-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-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
- 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 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001049165 Caria Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 239000004287 Dehydroacetic acid Substances 0.000 description 1
- 206010013710 Drug interaction Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 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
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010061876 Obstruction Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 201000005702 Pertussis Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DJADXQWEATYJRA-UHFFFAOYSA-N [4-[1-(5-acetyl-4,6-dihydroxy-2-oxopyran-3-yl)ethylideneamino]phenyl] acetate Chemical compound CC(=NC1=CC=C(C=C1)OC(=O)C)C2=C(C(=C(OC2=O)O)C(=O)C)O DJADXQWEATYJRA-UHFFFAOYSA-N 0.000 description 1
- RLMWJEFOZLQOMN-UHFFFAOYSA-N [4-[1-(5-acetyl-4-hydroxy-2,6-dioxopyran-3-ylidene)ethylamino]phenyl] hexanoate Chemical compound C1=CC(OC(=O)CCCCC)=CC=C1NC(C)=C1C(O)=C(C(C)=O)C(=O)OC1=O RLMWJEFOZLQOMN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 229940061632 dehydroacetic acid Drugs 0.000 description 1
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 description 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 1
- 235000019258 dehydroacetic acid Nutrition 0.000 description 1
- 229940057307 dihydrate calcium sulfate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 239000000499 gel 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
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 108010052322 limitin Proteins 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000006199 nebulizer Substances 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
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49264074A | 1974-07-29 | 1974-07-29 | |
| US57089675A | 1975-04-23 | 1975-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1064509A true CA1064509A (en) | 1979-10-16 |
Family
ID=27050812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA231,964A Expired CA1064509A (en) | 1974-07-29 | 1975-07-22 | Substituted 2h-pyran-2,6(3h)-dione derivatives |
Country Status (17)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1572271A (en) * | 1976-06-16 | 1980-07-30 | Smithkline Corp | 5-acetyl-4-hydroxy-(3(1-phenylaminoethylidene)-2h-pyran-2,6(3h)-dione derivatives |
| FR2388808A1 (fr) * | 1977-04-29 | 1978-11-24 | Smithkline Corp | Derives substitues de 2h-pyranne-2,6(3h)-diones, leur preparation et leur application en therapeutique |
| US4160021A (en) * | 1977-05-23 | 1979-07-03 | Smithkline Corporation | Substituted 2H-pyran-2,6(3H)-dione derivatives |
| US5263435A (en) * | 1992-08-12 | 1993-11-23 | Mitsuba Electric Manufacturing Co., Ltd. | Volute horn and method of manufacturing |
-
1975
- 1975-07-22 DK DK332675AA patent/DK134552B/da not_active IP Right Cessation
- 1975-07-22 CA CA231,964A patent/CA1064509A/en not_active Expired
- 1975-07-23 ES ES439664A patent/ES439664A1/es not_active Expired
- 1975-07-24 HU HU75SI1481A patent/HU174067B/hu unknown
- 1975-07-24 IE IE1663/75A patent/IE41709B1/en unknown
- 1975-07-24 FI FI752139A patent/FI59406C/fi not_active IP Right Cessation
- 1975-07-24 IL IL47792A patent/IL47792A/xx unknown
- 1975-07-24 GB GB30936/75A patent/GB1521712A/en not_active Expired
- 1975-07-25 FR FR7523296A patent/FR2280367A1/fr active Granted
- 1975-07-25 LU LU73066A patent/LU73066A1/xx unknown
- 1975-07-25 NO NO752638A patent/NO142668C/no unknown
- 1975-07-28 AT AT584475A patent/AT343657B/de not_active IP Right Cessation
- 1975-07-28 CH CH982875A patent/CH615433A5/de not_active IP Right Cessation
- 1975-07-29 DD DD187549A patent/DD118626A5/xx unknown
- 1975-07-29 JP JP50092974A patent/JPS5136458A/ja active Pending
- 1975-07-29 DE DE2533843A patent/DE2533843C2/de not_active Expired
- 1975-07-29 NL NL7509032A patent/NL7509032A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE41709B1 (en) | 1980-03-12 |
| JPS5136458A (en) | 1976-03-27 |
| ATA584475A (de) | 1977-10-15 |
| FI59406B (fi) | 1981-04-30 |
| FR2280367A1 (fr) | 1976-02-27 |
| ES439664A1 (es) | 1977-03-01 |
| NO142668B (no) | 1980-06-16 |
| AU8345075A (en) | 1977-02-03 |
| NO142668C (no) | 1980-09-24 |
| DE2533843C2 (de) | 1984-06-14 |
| NO752638L (enrdf_load_stackoverflow) | 1976-01-30 |
| IL47792A0 (en) | 1975-10-15 |
| FI752139A7 (enrdf_load_stackoverflow) | 1976-01-30 |
| NL7509032A (nl) | 1976-02-02 |
| LU73066A1 (enrdf_load_stackoverflow) | 1976-03-02 |
| FI59406C (fi) | 1981-08-10 |
| DK332675A (enrdf_load_stackoverflow) | 1976-01-30 |
| IL47792A (en) | 1978-06-15 |
| AT343657B (de) | 1978-06-12 |
| DK134552B (da) | 1976-11-29 |
| DE2533843A1 (de) | 1976-02-19 |
| IE41709L (en) | 1976-01-29 |
| DK134552C (enrdf_load_stackoverflow) | 1977-05-09 |
| CH615433A5 (en) | 1980-01-31 |
| HU174067B (hu) | 1979-10-28 |
| DD118626A5 (enrdf_load_stackoverflow) | 1976-03-12 |
| FR2280367B1 (enrdf_load_stackoverflow) | 1979-08-10 |
| GB1521712A (en) | 1978-08-16 |
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