CN1071925A - 新的3-(取代四唑基)-4-氧代-4H-吡啶并[1，2-a]嘧啶，它们的盐，含有它们的药物组合物及其制备方法 - Google Patents
新的3-(取代四唑基)-4-氧代-4H-吡啶并[1，2-a]嘧啶，它们的盐，含有它们的药物组合物及其制备方法 Download PDFInfo
- Publication number
- CN1071925A CN1071925A CN92110634A CN92110634A CN1071925A CN 1071925 A CN1071925 A CN 1071925A CN 92110634 A CN92110634 A CN 92110634A CN 92110634 A CN92110634 A CN 92110634A CN 1071925 A CN1071925 A CN 1071925A
- Authority
- CN
- China
- Prior art keywords
- oxo
- pyrido
- pyrimidine
- tetrazolium
- methyl
- 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.)
- Pending
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- 238000002360 preparation method Methods 0.000 title claims abstract description 47
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
- -1 3-(substituted tetrazolyl)-4-oxo-4H-pyrido[1,2-a]pyrimidines Chemical class 0.000 title description 8
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- 238000002425 crystallisation Methods 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 21
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- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
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- FDESMPVXUFITNN-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C=1N=C2C=CC=CN2C(=O)C=1C1=NN=NN1 FDESMPVXUFITNN-UHFFFAOYSA-N 0.000 description 11
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- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000001120 cytoprotective effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000011507 gypsum plaster Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- ZUZMMWXMHNDRLQ-UHFFFAOYSA-N methyl 5-(4-oxopyrido[1,2-a]pyrimidin-3-yl)tetrazole-1-carboxylate Chemical compound COC(=O)N1N=NN=C1C(C1=O)=CN=C2N1C=CC=C2 ZUZMMWXMHNDRLQ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- RQFLGKYCYMMRMC-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O RQFLGKYCYMMRMC-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000000247 postprecipitation Methods 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU620590A HU209793B (en) | 1990-09-25 | 1990-09-25 | Process for the production of pyrido[1,2-a]pyrimidine-derivatives and pharmaceutical compositions containing the same |
| HU6205/90 | 1991-08-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1071925A true CN1071925A (zh) | 1993-05-12 |
Family
ID=10971360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN92110634A Pending CN1071925A (zh) | 1990-09-25 | 1992-08-13 | 新的3-(取代四唑基)-4-氧代-4H-吡啶并[1，2-a]嘧啶，它们的盐，含有它们的药物组合物及其制备方法 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5475000A (enExample) |
| EP (1) | EP0641340A1 (enExample) |
| JP (1) | JPH06509800A (enExample) |
| CN (1) | CN1071925A (enExample) |
| AU (1) | AU663886B2 (enExample) |
| BG (1) | BG98448A (enExample) |
| CA (1) | CA2114145A1 (enExample) |
| CZ (1) | CZ27694A3 (enExample) |
| EE (1) | EE9400115A (enExample) |
| FI (1) | FI940591A7 (enExample) |
| HU (1) | HU209793B (enExample) |
| IL (1) | IL102788A (enExample) |
| MX (1) | MX9204659A (enExample) |
| PT (1) | PT100774A (enExample) |
| SI (1) | SI9200172A (enExample) |
| SK (1) | SK16594A3 (enExample) |
| TW (1) | TW222632B (enExample) |
| WO (1) | WO1993004065A1 (enExample) |
| YU (1) | YU76092A (enExample) |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055911A (en) * | 1958-04-29 | 1962-09-25 | William G Finnegan | Substituted tetrazoles |
| US4122274A (en) * | 1977-05-25 | 1978-10-24 | Bristol-Myers Company | 3-Tetrazolo-5,6,7,8-substituted-pyrido[1,2-a]pyrimidin-4-ones |
| JPS5536447A (en) * | 1978-09-07 | 1980-03-14 | Otsuka Pharmaceut Co Ltd | Butyramide derivative |
| US4432986A (en) * | 1979-06-18 | 1984-02-21 | Riker Laboratories, Inc. | Tetrazoles bonded to certain polycyclic aromatic systems and anti-allergic use thereof |
| US4474792A (en) * | 1979-06-18 | 1984-10-02 | Riker Laboratories, Inc. | N-Tetrazolyl benzamides and anti-allergic use thereof |
| FI73423C (fi) * | 1980-02-29 | 1987-10-09 | Otsuka Pharma Co Ltd | Foerfarande foer framstaellning av farmakologiskt verksamma tetrazolderivat. |
| US4457932A (en) * | 1983-07-22 | 1984-07-03 | Bristol-Myers Company | Anti-ulcer agents |
| FR2549831A1 (fr) * | 1983-07-27 | 1985-02-01 | Rhone Poulenc Agrochimie | Nouveaux derives d'acides aryloxybenzoiques, et leur utilisation comme herbicides |
| US4845227A (en) * | 1984-06-18 | 1989-07-04 | Eli Lilly And Company | Aromatase inhibitors from azoles |
| US5237070A (en) * | 1985-07-22 | 1993-08-17 | Riker Laboratories, Inc. | Substituted DI-t-butylphenols |
| US5049572A (en) * | 1987-04-06 | 1991-09-17 | Riker Laboratories, Inc. | Substituted di-t-butylphenols and anti-allergic use thereof |
| JP2668259B2 (ja) * | 1988-02-18 | 1997-10-27 | 塩野義製薬株式会社 | 複素環化合物および抗潰瘍剤 |
| HUT64064A (en) * | 1992-02-13 | 1993-11-29 | Chinoin Gyogyszer Es Vegyeszet | Process for producing puyrido/1,2-a/pyrimidine derivatives and pharmaceutical compositions comprising same as active ingredient |
-
1990
- 1990-09-25 HU HU620590A patent/HU209793B/hu not_active IP Right Cessation
-
1992
- 1992-08-07 YU YU76092A patent/YU76092A/sh unknown
- 1992-08-11 IL IL10278892A patent/IL102788A/en not_active IP Right Cessation
- 1992-08-12 MX MX9204659A patent/MX9204659A/es unknown
- 1992-08-13 US US08/193,080 patent/US5475000A/en not_active Expired - Fee Related
- 1992-08-13 CA CA002114145A patent/CA2114145A1/en not_active Abandoned
- 1992-08-13 SK SK165-94A patent/SK16594A3/sk unknown
- 1992-08-13 JP JP5504219A patent/JPH06509800A/ja active Pending
- 1992-08-13 PT PT100774A patent/PT100774A/pt not_active Application Discontinuation
- 1992-08-13 AU AU24628/92A patent/AU663886B2/en not_active Ceased
- 1992-08-13 WO PCT/HU1992/000031 patent/WO1993004065A1/en not_active Ceased
- 1992-08-13 EP EP92917915A patent/EP0641340A1/en not_active Withdrawn
- 1992-08-13 SI SI19929200172A patent/SI9200172A/sl unknown
- 1992-08-13 CN CN92110634A patent/CN1071925A/zh active Pending
- 1992-09-19 TW TW081107387A patent/TW222632B/zh active
-
1994
- 1994-02-09 FI FI940591A patent/FI940591A7/fi not_active Application Discontinuation
- 1994-02-09 CZ CZ94276A patent/CZ27694A3/cs unknown
- 1994-02-10 BG BG98448A patent/BG98448A/xx unknown
- 1994-08-10 EE EE9400115A patent/EE9400115A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUT64954A (en) | 1994-03-28 |
| TW222632B (enExample) | 1994-04-21 |
| JPH06509800A (ja) | 1994-11-02 |
| BG98448A (bg) | 1994-11-15 |
| EE9400115A (et) | 1995-12-15 |
| IL102788A (en) | 1996-03-31 |
| SK16594A3 (en) | 1994-08-10 |
| SI9200172A (en) | 1993-03-31 |
| HU906205D0 (en) | 1991-03-28 |
| YU76092A (sr) | 1996-01-09 |
| FI940591A0 (fi) | 1994-02-09 |
| MX9204659A (es) | 1993-12-31 |
| AU663886B2 (en) | 1995-10-26 |
| EP0641340A1 (en) | 1995-03-08 |
| CZ27694A3 (en) | 1994-08-17 |
| CA2114145A1 (en) | 1993-03-04 |
| FI940591A7 (fi) | 1994-02-09 |
| US5475000A (en) | 1995-12-12 |
| WO1993004065A1 (en) | 1993-03-04 |
| AU2462892A (en) | 1993-03-16 |
| PT100774A (pt) | 1993-10-29 |
| HU209793B (en) | 1994-11-28 |
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| C06 | Publication | ||
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| SE01 | Entry into force of request for substantive examination | ||
| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |