FI57408C - Foerfarande foer framstaellning av antiallergiska 3-(tetrazol-5-yl)-kromoner - Google Patents
Foerfarande foer framstaellning av antiallergiska 3-(tetrazol-5-yl)-kromoner Download PDFInfo
- Publication number
- FI57408C FI57408C FI1160/73A FI116073A FI57408C FI 57408 C FI57408 C FI 57408C FI 1160/73 A FI1160/73 A FI 1160/73A FI 116073 A FI116073 A FI 116073A FI 57408 C FI57408 C FI 57408C
- Authority
- FI
- Finland
- Prior art keywords
- parts
- tetrazol
- added
- mixture
- tetrahydrofuran
- Prior art date
Links
- 230000003266 anti-allergic effect Effects 0.000 title claims description 7
- -1 TETRAZOLE-5-YL Chemical class 0.000 title description 26
- 238000005057 refrigeration Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 49
- 238000002844 melting Methods 0.000 claims description 25
- 230000008018 melting Effects 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
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- HJOBCUUZGWRLTO-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)chromen-4-one Chemical class C=1OC2=CC=CC=C2C(=O)C=1C=1N=NNN=1 HJOBCUUZGWRLTO-UHFFFAOYSA-N 0.000 claims description 7
- 229910017604 nitric acid Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
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- 150000002431 hydrogen Chemical class 0.000 claims 3
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- 150000001721 carbon Chemical group 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- UUXFWHMUNNXFHD-UHFFFAOYSA-N barium azide Chemical compound [Ba+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] UUXFWHMUNNXFHD-UHFFFAOYSA-N 0.000 description 1
- 238000010170 biological method Methods 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- UETLMBWMVIQIGU-UHFFFAOYSA-N calcium azide Chemical compound [Ca+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] UETLMBWMVIQIGU-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229960000520 diphenhydramine Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- HRIKRJRMQIBSTO-UHFFFAOYSA-N ethyl 3-cyano-4-oxochromene-6-carboxylate Chemical compound O1C=C(C#N)C(=O)C2=CC(C(=O)OCC)=CC=C21 HRIKRJRMQIBSTO-UHFFFAOYSA-N 0.000 description 1
- MVUXRJGLKUEIRM-UHFFFAOYSA-N ethyl 4-oxo-3-(2h-tetrazol-5-yl)chromene-6-carboxylate Chemical compound O=C1C2=CC(C(=O)OCC)=CC=C2OC=C1C1=NN=NN1 MVUXRJGLKUEIRM-UHFFFAOYSA-N 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- TWRAJPCQPHBABR-UHFFFAOYSA-N magnesium;diazide Chemical compound [Mg+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] TWRAJPCQPHBABR-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 1
- 229960002221 methylephedrine Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940066827 pertussis vaccine Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229960003910 promethazine Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 231100000121 skin sensitizing Toxicity 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- PDEROVFZLWBVSG-UHFFFAOYSA-N strontium;diazide Chemical compound [Sr+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] PDEROVFZLWBVSG-UHFFFAOYSA-N 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- PCTNAMGLSYHIPL-UHFFFAOYSA-N tin(4+) tetraazide Chemical compound [Sn+4].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-] PCTNAMGLSYHIPL-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- UBKFNPJMWUJHGB-UHFFFAOYSA-N titanium(4+);tetraazide Chemical compound [Ti+4].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-] UBKFNPJMWUJHGB-UHFFFAOYSA-N 0.000 description 1
- 229960003223 tripelennamine Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- QFDUTPNKBRXHTC-UHFFFAOYSA-N zinc diazide Chemical compound [Zn++].[N-]=[N+]=[N-].[N-]=[N+]=[N-] QFDUTPNKBRXHTC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI792810A FI792810A (fi) | 1972-04-12 | 1979-09-10 | Kromonderivat |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3723572 | 1972-04-12 | ||
| JP47037235A JPS5118955B2 (ro) | 1972-04-12 | 1972-04-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI57408B FI57408B (fi) | 1980-04-30 |
| FI57408C true FI57408C (fi) | 1980-08-11 |
Family
ID=12491931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI1160/73A FI57408C (fi) | 1972-04-12 | 1973-04-12 | Foerfarande foer framstaellning av antiallergiska 3-(tetrazol-5-yl)-kromoner |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3896114A (ro) |
| JP (1) | JPS5118955B2 (ro) |
| AT (1) | AT323739B (ro) |
| AU (1) | AU470496B2 (ro) |
| BE (1) | BE798059A (ro) |
| CA (1) | CA1006160A (ro) |
| CH (3) | CH605891A5 (ro) |
| CS (2) | CS185639B2 (ro) |
| DE (1) | DE2317899A1 (ro) |
| ES (2) | ES413577A1 (ro) |
| FI (1) | FI57408C (ro) |
| FR (2) | FR2182951B1 (ro) |
| GB (2) | GB1417461A (ro) |
| HU (2) | HU167386B (ro) |
| NL (1) | NL7305020A (ro) |
| NO (2) | NO137825C (ro) |
| PH (2) | PH13020A (ro) |
| PL (1) | PL89172B1 (ro) |
| SE (2) | SE402291B (ro) |
| SU (2) | SU500758A3 (ro) |
| ZA (1) | ZA732526B (ro) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1540391A (en) * | 1975-04-11 | 1979-02-14 | Takeda Chemical Industries Ltd | 3-(1h-tetrazol-5-yl)-chromone derivatives |
| US4033845A (en) * | 1975-11-20 | 1977-07-05 | Warner-Lambert Company | [2-(4-Oxo-4H-1-benzopyran-2-yl)ethenyl]benzonitriles and benzoic acids |
| GB1560489A (en) * | 1976-05-21 | 1980-02-06 | Fisons Ltd | Pharmaceutical compositions |
| AU508350B2 (en) * | 1976-06-16 | 1980-03-20 | Farmitalia Carlo Erba S.P.A. | Substicuted 2-vinyl-chromones |
| US4183946A (en) * | 1976-06-16 | 1980-01-15 | Carlo Erba S.P.A. | Substituted 2-vinyl-chromones and process for their preparation |
| US4183945A (en) * | 1976-06-16 | 1980-01-15 | Carlo Erba S.P.A. | Substituted 2-vinyl-chromones and process for their preparation |
| US4177276A (en) * | 1976-06-16 | 1979-12-04 | Farmitalia Carlo Erba, S.P.A. | Substituted 2-vinyl-chromones and process for their preparation |
| US4143145A (en) * | 1977-01-12 | 1979-03-06 | Carlo Erba S. P. A. | Substituted 2-vinyl-chromones and process for their preparation |
| US4116971A (en) * | 1977-08-15 | 1978-09-26 | Warner-Lambert Company | 3-(1h-tetrazol-5-yl)chromones |
| US4360527A (en) * | 1977-10-13 | 1982-11-23 | Warner-Lambert Company | 9-(Hydroxy, lower alkoxy or lower alkanoyloxy)-2-(1H-tetrazol-5-yl)naphtho-(2,1-b)-pyran-1-ones and anti-allergic use thereof |
| DE2840936C2 (de) * | 1978-09-20 | 1983-02-10 | Warner-Lambert Co., 07950 Morris Plains, N.J. | 3-(1H-Tetrazol-5-yl)-chromone und ihre Verwendung |
| DE3070912D1 (en) * | 1979-03-20 | 1985-09-05 | Fisons Plc | Pharmaceutical heterocyclic compounds, processes for their preparation and compositions containing them |
| ZA804788B (en) * | 1979-10-26 | 1981-07-29 | Erba Farmitalia | Substituted 2-(pyridyl-cyclopropyl)-chromones and process for their preparation |
| JP2004323392A (ja) * | 2003-04-23 | 2004-11-18 | Toyo Kasei Kogyo Co Ltd | ビテトラゾールアミン化合物の製造方法 |
| GB201506572D0 (en) | 2015-04-17 | 2015-06-03 | Johnson Matthey Davy Technologies Ltd | Process |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA960223A (en) * | 1970-02-05 | 1974-12-31 | Mervyn E. Peel | Tetrazolyl chromones |
-
1972
- 1972-04-12 JP JP47037235A patent/JPS5118955B2/ja not_active Expired
-
1973
- 1973-04-05 AU AU54132/73A patent/AU470496B2/en not_active Expired
- 1973-04-10 PL PL1973161818A patent/PL89172B1/pl unknown
- 1973-04-10 DE DE2317899A patent/DE2317899A1/de not_active Withdrawn
- 1973-04-10 US US349848A patent/US3896114A/en not_active Expired - Lifetime
- 1973-04-10 FR FR7312922A patent/FR2182951B1/fr not_active Expired
- 1973-04-10 NL NL7305020A patent/NL7305020A/xx not_active Application Discontinuation
- 1973-04-11 BE BE129880A patent/BE798059A/xx unknown
- 1973-04-11 CS CS7500001198A patent/CS185639B2/cs unknown
- 1973-04-11 PH PH14507A patent/PH13020A/en unknown
- 1973-04-11 ES ES413577A patent/ES413577A1/es not_active Expired
- 1973-04-11 SU SU1913752A patent/SU500758A3/ru active
- 1973-04-11 CS CS7300002571A patent/CS185620B2/cs unknown
- 1973-04-11 CA CA168,432A patent/CA1006160A/en not_active Expired
- 1973-04-11 SE SE7305124A patent/SE402291B/xx unknown
- 1973-04-11 NO NO1505/73A patent/NO137825C/no unknown
- 1973-04-12 HU HUTA1246A patent/HU167386B/hu unknown
- 1973-04-12 GB GB1760273A patent/GB1417461A/en not_active Expired
- 1973-04-12 GB GB1497275A patent/GB1417462A/en not_active Expired
- 1973-04-12 CH CH127977A patent/CH605891A5/xx not_active IP Right Cessation
- 1973-04-12 ZA ZA732526A patent/ZA732526B/xx unknown
- 1973-04-12 AT AT325073A patent/AT323739B/de not_active IP Right Cessation
- 1973-04-12 CH CH523773A patent/CH582174A5/xx not_active IP Right Cessation
- 1973-04-12 CH CH921976A patent/CH603616A5/xx not_active IP Right Cessation
- 1973-04-12 HU HUTA1333A patent/HU168124B/hu unknown
- 1973-04-12 FI FI1160/73A patent/FI57408C/fi active
-
1974
- 1974-10-11 NO NO743670A patent/NO141556C/no unknown
- 1974-12-19 ES ES0433109A patent/ES433109A1/es not_active Expired
-
1975
- 1975-01-17 SU SU752099318A patent/SU745367A3/ru active
- 1975-04-10 FR FR7511248A patent/FR2273003B1/fr not_active Expired
-
1976
- 1976-02-18 SE SE7601868A patent/SE7601868L/xx unknown
-
1977
- 1977-07-21 PH PH20019A patent/PH13114A/en unknown
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