CH615433A5 - Process for the preparation of 2H-pyrane-2,6(3H)-dione derivatives and salts thereof - Google Patents

Process for the preparation of 2H-pyrane-2,6(3H)-dione derivatives and salts thereof Download PDF

Info

Publication number: CH615433A5
Authority: CH; Switzerland
Prior art keywords: pyran; dione; radical; acetyl; hydroxy
Prior art date: 1974-07-29

Application number

CH982875A

Other languages

German (de)

English (en)

Inventor

Lawrence William Chakrin

Kenneth Means Snader

Chester Rhodes Willis

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.)

1974-07-29

Filing date

1975-07-28

Publication date

1980-01-31

1975-07-28 Application filed by Smithkline Corp filed Critical Smithkline Corp

1980-01-31 Publication of CH615433A5 publication Critical patent/CH615433A5/de

Links

238000000034 method Methods 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 8
150000003839 salts Chemical class 0.000 title claims description 6
SYIUWAVTBADRJG-UHFFFAOYSA-N 2H-pyran-2,6(3H)-dione Chemical class O=C1CC=CC(=O)O1 SYIUWAVTBADRJG-UHFFFAOYSA-N 0.000 title claims description 3
230000008569 process Effects 0.000 title claims description 3
-1 alkyl radical Chemical group 0.000 claims description 31
150000001875 compounds Chemical class 0.000 claims description 29
238000010992 reflux Methods 0.000 claims description 16
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 15
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 8
OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 claims description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
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 claims description 3
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 3
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 2
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims 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 claims description 2
239000002253 acid Substances 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims 3
125000004432 carbon atom Chemical group C* 0.000 claims 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
GPKUICFDWYEPTK-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=CC=C=C[CH]1 GPKUICFDWYEPTK-UHFFFAOYSA-N 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 18
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 17
239000003814 drug Substances 0.000 description 13
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239000000203 mixture Substances 0.000 description 10
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
230000005764 inhibitory process Effects 0.000 description 8
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
238000002844 melting Methods 0.000 description 5
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NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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238000001953 recrystallisation Methods 0.000 description 4
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125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 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
239000003085 diluting agent Substances 0.000 description 3
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239000007788 liquid Substances 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
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239000011541 reaction mixture Substances 0.000 description 3
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239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
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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
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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
230000015572 biosynthetic process Effects 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
239000004615 ingredient Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 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
230000004044 response Effects 0.000 description 2
229940076279 serotonin Drugs 0.000 description 2
239000002904 solvent Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000006188 syrup Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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
YAEZNHYOZHLAHC-UHFFFAOYSA-N (4-aminophenyl) n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=CC=C(N)C=C1 YAEZNHYOZHLAHC-UHFFFAOYSA-N 0.000 description 1
JFANLKHJWWLSAT-UHFFFAOYSA-N (4-aminophenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=C(N)C=C1 JFANLKHJWWLSAT-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
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-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
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-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
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
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
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 1
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 description 1
244000215068 Acacia senegal Species 0.000 description 1
229920001817 Agar Polymers 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
239000005995 Aluminium silicate Substances 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
102000004506 Blood Proteins Human genes 0.000 description 1
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101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
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108010058846 Ovalbumin Proteins 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
FNFIMLQNUVUTBD-UHFFFAOYSA-N [4-[1-(5-acetyl-4-hydroxy-2,6-dioxopyran-3-ylidene)ethylamino]phenyl] butanoate Chemical compound C1=CC(OC(=O)CCC)=CC=C1NC(C)=C1C(O)=C(C(C)=O)C(=O)OC1=O FNFIMLQNUVUTBD-UHFFFAOYSA-N 0.000 description 1
FWKZXFQMOSHIJW-UHFFFAOYSA-N [4-[1-(5-acetyl-4-hydroxy-2,6-dioxopyran-3-ylidene)ethylamino]phenyl] pentanoate Chemical compound C1=CC(OC(=O)CCCC)=CC=C1NC(C)=C1C(O)=C(C(C)=O)C(=O)OC1=O FWKZXFQMOSHIJW-UHFFFAOYSA-N 0.000 description 1
KLXQOHSHYKVPJI-UHFFFAOYSA-N [4-[1-(5-acetyl-4-hydroxy-2,6-dioxopyran-3-ylidene)ethylamino]phenyl] propanoate Chemical compound C1=CC(OC(=O)CC)=CC=C1NC(C)=C1C(O)=C(C(C)=O)C(=O)OC1=O KLXQOHSHYKVPJI-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
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235000010419 agar Nutrition 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
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230000005875 antibody response Effects 0.000 description 1
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230000004071 biological effect Effects 0.000 description 1
239000001045 blue dye Substances 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
230000004856 capillary permeability Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
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239000003795 chemical substances by application Substances 0.000 description 1
239000007910 chewable tablet Substances 0.000 description 1
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PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
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230000003993 interaction Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
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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
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XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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239000007858 starting material Substances 0.000 description 1
238000011282 treatment Methods 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
238000012982 x-ray structure analysis 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)

CH982875A 1974-07-29 1975-07-28 Process for the preparation of 2H-pyrane-2,6(3H)-dione derivatives and salts thereof CH615433A5 (en)

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
CH615433A5 true CH615433A5 (en)	1980-01-31

Family

ID=27050812

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH982875A CH615433A5 (en)	1974-07-29	1975-07-28	Process for the preparation of 2H-pyrane-2,6(3H)-dione derivatives and salts thereof

Country Status (17)

Country	Link
JP (1)	JPS5136458A (da)
AT (1)	AT343657B (da)
CA (1)	CA1064509A (da)
CH (1)	CH615433A5 (da)
DD (1)	DD118626A5 (da)
DE (1)	DE2533843C2 (da)
DK (1)	DK134552B (da)
ES (1)	ES439664A1 (da)
FI (1)	FI59406C (da)
FR (1)	FR2280367A1 (da)
GB (1)	GB1521712A (da)
HU (1)	HU174067B (da)
IE (1)	IE41709B1 (da)
IL (1)	IL47792A (da)
LU (1)	LU73066A1 (da)
NL (1)	NL7509032A (da)
NO (1)	NO142668C (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
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 IL IL47792A patent/IL47792A/xx unknown
- 1975-07-24 FI FI752139A patent/FI59406C/fi not_active IP Right Cessation
- 1975-07-24 GB GB30936/75A patent/GB1521712A/en not_active Expired
- 1975-07-24 IE IE1663/75A patent/IE41709B1/en unknown
- 1975-07-24 HU HU75SI1481A patent/HU174067B/hu unknown
- 1975-07-25 FR FR7523296A patent/FR2280367A1/fr active Granted
- 1975-07-25 NO NO752638A patent/NO142668C/no unknown
- 1975-07-25 LU LU73066A patent/LU73066A1/xx unknown
- 1975-07-28 CH CH982875A patent/CH615433A5/de not_active IP Right Cessation
- 1975-07-28 AT AT584475A patent/AT343657B/de not_active IP Right Cessation
- 1975-07-29 DD DD187549A patent/DD118626A5/xx unknown
- 1975-07-29 NL NL7509032A patent/NL7509032A/xx unknown
- 1975-07-29 JP JP50092974A patent/JPS5136458A/ja active Pending
- 1975-07-29 DE DE2533843A patent/DE2533843C2/de not_active Expired

Also Published As

Publication number	Publication date
CA1064509A (en)	1979-10-16
FR2280367A1 (fr)	1976-02-27
DK134552C (da)	1977-05-09
DD118626A5 (da)	1976-03-12
IE41709L (en)	1976-01-29
NO752638L (da)	1976-01-30
FI752139A (da)	1976-01-30
FI59406B (fi)	1981-04-30
GB1521712A (en)	1978-08-16
JPS5136458A (en)	1976-03-27
ATA584475A (de)	1977-10-15
ES439664A1 (es)	1977-03-01
DE2533843A1 (de)	1976-02-19
NO142668C (no)	1980-09-24
NO142668B (no)	1980-06-16
AT343657B (de)	1978-06-12
DK134552B (da)	1976-11-29
FR2280367B1 (da)	1979-08-10
IL47792A0 (en)	1975-10-15
HU174067B (hu)	1979-10-28
AU8345075A (en)	1977-02-03
LU73066A1 (da)	1976-03-02
DE2533843C2 (de)	1984-06-14
IE41709B1 (en)	1980-03-12
NL7509032A (nl)	1976-02-02
IL47792A (en)	1978-06-15
FI59406C (fi)	1981-08-10
DK332675A (da)	1976-01-30

Publication	Publication Date	Title
DE2362409C3 (de)	1980-05-14	N,N'-(m-Phenylen)-dioxamidsäuren und deren Derivate, Verfahren zu ihrer Herstellung und Arzneimittel, die diese Verbindungen enthalten
DE2847792C2 (da)	1988-02-04
DE2428486A1 (de)	1975-01-09	Azapurinone
DE2653257A1 (de)	1977-06-02	Neue kondensierte pyrimidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als entzuendungshemmende und die gerinnung des blutes hemmende arzneimittel
DE2263100C2 (de)	1986-01-30	5,5-Dimethyl-8-(3-methyl-2-octyl)-10-[4-(piperidino)-butyryloxy]-2-(2-propinyl)-1,2,3,4-tetrahydro-5H-[1]-benzopyrano[3,4-d]pyridin, Verfahren zu dessen Herstellung und die Verbindung enthaltende Arzneimittel
DE1445675C3 (de)	1974-02-28	Pyridylharnstoffe und Verfahren zu ihrer Herstellung
DE2025080A1 (de)	1970-11-26	Neue Melaminderivate und ihre Herstellung
CH615433A5 (en)	1980-01-31	Process for the preparation of 2H-pyrane-2,6(3H)-dione derivatives and salts thereof
DE3882785T2 (de)	1994-01-27	Di-t-butylphenylalkyl- und benzyläther.
CH628887A5 (de)	1982-03-31	Verfahren zur herstellung von benzolsulfonylharnstoffen.
DE2525249C2 (de)	1984-04-26	N,N'-(m-Phenylen)-dioxamsäuren und deren Derivate, Verfahren zur Herstellung derselben und dieselben enthaltende pharmazeutische Präparate
DE2727207C2 (de)	1986-10-23	Substituierte 2H-Pyran-2,6(3H)-dion-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2511316A1 (de)	1975-09-18	Imidazo-eckige klammer auf 1,2 c eckige klammer zu -pyrimidinderivate, verfahren zu deren herstellung und deren verwendung
DE2641291C2 (de)	1986-07-24	2-cyano-3- oder 4-(substituiertes amino)-oxanilsaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
DE2649855C2 (de)	1987-01-22	Substituierte 5-Acetyl-4-hydroxy-3-phenylamino-2H-pyran-2,6(3H)-dione, Verfahren zu deren Herstellung und deren Verwendung
DE2914052C2 (da)	1990-04-26
DE2424076A1 (de)	1974-12-05	Derivate von 4-hydroxy-3-nitrocarbostyrilen enthaltende arzneimittel, neue 4-hydroxy-3-nitrocarbostyrile und verfahren zu ihrer herstellung
DE2445002A1 (de)	1975-04-10	Pyridin-diyl-dioxamsaeuren und deren pharmazeutisch vertraegliche saeureadditionssalze, verfahren zu deren herstellung und dieselben enthaltende pharmazeutische mittel
DE2244737B2 (de)	1978-06-01	H-o-ChlorphenyD-2-tert-butylaminoäthanol, Verfahren zu dessen Herstellung und Arzneimittel auf dessen Basis
DE2550647A1 (de)	1976-05-20	Arzneipraeparate mit einem gehalt an 4,6-dihydroxy-2h-pyran-2-onen
DE2821947A1 (de)	1978-11-30	2h-pyran-2,6(3h)-dion-derivate
DE3111522C2 (da)	1989-05-18
DE2609574B2 (de)	1977-10-27	1-(4-fluor-3-trifluormethylthio- phenyl)-piperazin, dessen salze, verfahren zu dessen herstellung und arzneimittel
DE3414049A1 (de)	1984-10-18	Pharmazeutisches mittel und dessen verwendung zur behandlung der nephritis
DE2818984A1 (de)	1978-11-02	2h-pyran-2,6(3h)-dione und ihre alkalimetallsalze sowie verfahren zu ihrer herstellung

Legal Events

Date	Code	Title	Description
1987-03-31	PL	Patent ceased
2024-10-31	PL	Patent ceased