NO841157L - Fremgangsmaate ved fremstilling av nye (1h-tetrazol-5-yl)-2(1h)-kinoliner - Google Patents
Fremgangsmaate ved fremstilling av nye (1h-tetrazol-5-yl)-2(1h)-kinolinerInfo
- Publication number
- NO841157L NO841157L NO841157A NO841157A NO841157L NO 841157 L NO841157 L NO 841157L NO 841157 A NO841157 A NO 841157A NO 841157 A NO841157 A NO 841157A NO 841157 L NO841157 L NO 841157L
- Authority
- NO
- Norway
- Prior art keywords
- quinolinone
- cyano
- tetrazol
- reacted
- ammonium chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- -1 1H-TETRAZOL-5-YL Chemical class 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 26
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- WNRMLIGSXULUPQ-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carbonitrile Chemical compound C1=CC=C2C=C(C#N)C(=O)NC2=C1 WNRMLIGSXULUPQ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 235000019270 ammonium chloride Nutrition 0.000 claims abstract description 13
- 239000000243 solution Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000012442 inert solvent Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- HPOFGMVVGWXUBK-UHFFFAOYSA-N 3-(2H-tetrazol-5-yl)-1H-quinolin-2-one Chemical compound O=C1NC2=CC=CC=C2C=C1C1=NN=NN1 HPOFGMVVGWXUBK-UHFFFAOYSA-N 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000003536 tetrazoles Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- XHQPJFYUICYHHN-UHFFFAOYSA-N 1-methyl-2-oxoquinoline-3-carbonitrile Chemical compound C1=CC=C2C=C(C#N)C(=O)N(C)C2=C1 XHQPJFYUICYHHN-UHFFFAOYSA-N 0.000 claims description 2
- SECXAGBVQSKFMO-UHFFFAOYSA-N 1-methyl-3-(2h-tetrazol-5-yl)quinolin-2-one Chemical compound O=C1N(C)C2=CC=CC=C2C=C1C1=NN=NN1 SECXAGBVQSKFMO-UHFFFAOYSA-N 0.000 claims description 2
- HUWKQMRNPHUGMK-UHFFFAOYSA-N 2-oxo-1h-1,8-naphthyridine-3-carbonitrile Chemical compound C1=CC=C2C=C(C#N)C(O)=NC2=N1 HUWKQMRNPHUGMK-UHFFFAOYSA-N 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- RPYGMZBSPGKWMR-UHFFFAOYSA-N 2-oxoquinoline-1-carbonitrile Chemical compound C1=CC=C2N(C#N)C(=O)C=CC2=C1 RPYGMZBSPGKWMR-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- WPZVLGZVNGNCJN-UHFFFAOYSA-N 1-(2h-tetrazol-5-yl)quinolin-2-one Chemical class O=C1C=CC2=CC=CC=C2N1C1=NN=NN1 WPZVLGZVNGNCJN-UHFFFAOYSA-N 0.000 abstract 1
- 239000000043 antiallergic agent Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 32
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
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- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 229930185107 quinolinone Natural products 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pulmonology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/478,965 US4735948A (en) | 1983-03-25 | 1983-03-25 | (1H-tetrazol-5-yl)-2(1H)-quinolinones and-naphthyridones and antiallergic use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO841157L true NO841157L (no) | 1984-09-26 |
Family
ID=23902120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO841157A NO841157L (no) | 1983-03-25 | 1984-03-23 | Fremgangsmaate ved fremstilling av nye (1h-tetrazol-5-yl)-2(1h)-kinoliner |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4735948A (es) |
| EP (1) | EP0120483B1 (es) |
| JP (1) | JPS59176276A (es) |
| KR (1) | KR900003650B1 (es) |
| AT (1) | ATE26276T1 (es) |
| AU (1) | AU562115B2 (es) |
| CA (1) | CA1241001A (es) |
| DE (1) | DE3462895D1 (es) |
| DK (1) | DK163238C (es) |
| ES (1) | ES8601963A1 (es) |
| GR (1) | GR81908B (es) |
| IE (1) | IE57073B1 (es) |
| IL (1) | IL71319A (es) |
| NO (1) | NO841157L (es) |
| NZ (1) | NZ207581A (es) |
| PT (1) | PT78289B (es) |
| ZA (1) | ZA842065B (es) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT79031B (en) * | 1983-08-20 | 1986-08-22 | Boots Co Plc | Therapeutic agents |
| US5358949A (en) * | 1986-03-05 | 1994-10-25 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives and salts thereof and anti-arrhythmic agents containing the carbostyril derivatives |
| US4916131A (en) * | 1986-10-15 | 1990-04-10 | Schering Corporation | Naphthyridine derivatives and method for treating allergic reactions |
| EP0267691A3 (en) * | 1986-10-15 | 1989-08-23 | Schering Corporation | Use of 1-substituted naphthyridine and pyridopyrazine derivatives for the preparation of medicaments with immunosuppressor activity. |
| US5037826A (en) * | 1986-10-15 | 1991-08-06 | Schering Corporation | 1-substituted naphthyridine and pyridopyrazine derivatives |
| US5064837A (en) * | 1989-11-13 | 1991-11-12 | Schering Corporation | 3-substituted-1-aryl-2(h)-quinolones and their pharmaceutical compositions |
| GB9026389D0 (en) * | 1990-12-05 | 1991-01-23 | Merck Sharp & Dohme | Therapeutic agents |
| GB9125485D0 (en) * | 1991-11-29 | 1992-01-29 | Merck Sharp & Dohme | Therapeutic agents |
| WO1994012499A1 (en) * | 1992-12-01 | 1994-06-09 | The Green Cross Corporation | 1,8-naphthyridin-2-one derivative and use thereof_ |
| DE19727410A1 (de) * | 1997-06-27 | 1999-01-07 | Hoechst Schering Agrevo Gmbh | 3-(5-Tetrazolylcarbonyl)-2-chinolone und diese enthaltende nutzpflanzenschützende Mittel |
| GB0316546D0 (en) | 2003-07-15 | 2003-08-20 | Novartis Ag | Process for the manufacture of organic compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1444369A (en) * | 1973-04-05 | 1976-07-28 | Allen & Hanburys Ltd | 1,8-naphthyridines |
| US3993656A (en) * | 1974-11-19 | 1976-11-23 | Merck & Co., Inc. | 1,8-Naphthyridine compounds |
| US4035368A (en) * | 1975-04-02 | 1977-07-12 | Riker Laboratories, Inc. | Substituted 3-(1H-tetrazol-5-yl)-quinoline compounds |
| US4350817A (en) * | 1980-02-28 | 1982-09-21 | American Home Products Corporation | 4-Cl, Br or I-3-Carboxy or cyano-1,2-dihydro-2-oxo-1,8-naphthyridine derivatives |
| ES8608874A1 (es) * | 1984-05-29 | 1986-09-01 | Pfizer | Un procedimiento para la preparacion de una 2-(1h)-quinolona |
-
1983
- 1983-03-25 US US06/478,965 patent/US4735948A/en not_active Expired - Lifetime
-
1984
- 1984-03-20 CA CA000449959A patent/CA1241001A/en not_active Expired
- 1984-03-20 ZA ZA842065A patent/ZA842065B/xx unknown
- 1984-03-21 NZ NZ207581A patent/NZ207581A/en unknown
- 1984-03-21 GR GR74164A patent/GR81908B/el unknown
- 1984-03-21 PT PT78289A patent/PT78289B/pt not_active IP Right Cessation
- 1984-03-21 AU AU25952/84A patent/AU562115B2/en not_active Ceased
- 1984-03-22 ES ES530877A patent/ES8601963A1/es not_active Expired
- 1984-03-22 IL IL71319A patent/IL71319A/xx unknown
- 1984-03-22 JP JP59053691A patent/JPS59176276A/ja active Granted
- 1984-03-23 DE DE8484103231T patent/DE3462895D1/de not_active Expired
- 1984-03-23 IE IE720/84A patent/IE57073B1/en not_active IP Right Cessation
- 1984-03-23 DK DK165684A patent/DK163238C/da not_active IP Right Cessation
- 1984-03-23 EP EP84103231A patent/EP0120483B1/en not_active Expired
- 1984-03-23 NO NO841157A patent/NO841157L/no unknown
- 1984-03-23 AT AT84103231T patent/ATE26276T1/de active
- 1984-03-24 KR KR1019840001514A patent/KR900003650B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES530877A0 (es) | 1985-11-01 |
| EP0120483A1 (en) | 1984-10-03 |
| IE57073B1 (en) | 1992-04-22 |
| NZ207581A (en) | 1987-01-23 |
| PT78289B (en) | 1986-04-22 |
| PT78289A (en) | 1984-04-01 |
| EP0120483B1 (en) | 1987-04-01 |
| DK165684D0 (da) | 1984-03-23 |
| ATE26276T1 (de) | 1987-04-15 |
| DE3462895D1 (de) | 1987-05-07 |
| AU2595284A (en) | 1984-09-27 |
| GR81908B (es) | 1984-12-12 |
| ES8601963A1 (es) | 1985-11-01 |
| JPS59176276A (ja) | 1984-10-05 |
| IL71319A (en) | 1988-03-31 |
| AU562115B2 (en) | 1987-05-28 |
| DK163238C (da) | 1992-06-29 |
| ZA842065B (en) | 1984-10-31 |
| DK163238B (da) | 1992-02-10 |
| IL71319A0 (en) | 1984-06-29 |
| US4735948A (en) | 1988-04-05 |
| KR840008153A (ko) | 1984-12-13 |
| KR900003650B1 (ko) | 1990-05-28 |
| DK165684A (da) | 1984-09-26 |
| JPH0452273B2 (es) | 1992-08-21 |
| IE840720L (en) | 1984-09-25 |
| CA1241001A (en) | 1988-08-23 |
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