CN1039010C - 噁二唑基取代的二氮杂萘衍生物、其中间体、其制法及其药物组合物和其在制药中的应用 - Google Patents
噁二唑基取代的二氮杂萘衍生物、其中间体、其制法及其药物组合物和其在制药中的应用 Download PDFInfo
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- CN1039010C CN1039010C CN93116801A CN93116801A CN1039010C CN 1039010 C CN1039010 C CN 1039010C CN 93116801 A CN93116801 A CN 93116801A CN 93116801 A CN93116801 A CN 93116801A CN 1039010 C CN1039010 C CN 1039010C
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- tetrahydro
- compound
- pharmaceutically acceptable
- benzyl
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
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- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 18
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- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 11
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
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- RDLHKAMUCBURMC-UHFFFAOYSA-N 6-benzyl-3-(5-ethyl-1,2,4-oxadiazol-3-yl)-1,5,7,8-tetrahydro-1,6-naphthyridin-2-one Chemical compound O1C(CC)=NC(C=2C(NC=3CCN(CC=4C=CC=CC=4)CC=3C=2)=O)=N1 RDLHKAMUCBURMC-UHFFFAOYSA-N 0.000 claims 1
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- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
- HZZOEADXZLYIHG-UHFFFAOYSA-N magnesiomagnesium Chemical compound [Mg][Mg] HZZOEADXZLYIHG-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- WFJRIDQGVSJLLH-UHFFFAOYSA-N methyl n-aminocarbamate Chemical compound COC(=O)NN WFJRIDQGVSJLLH-UHFFFAOYSA-N 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- RARLPRMZJNIQGU-UHFFFAOYSA-N naphthalene-2-carbohydrazide Chemical compound C1=CC=CC2=CC(C(=O)NN)=CC=C21 RARLPRMZJNIQGU-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 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
- 229910052700 potassium Chemical group 0.000 description 1
- 239000011591 potassium Chemical group 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository 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
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000003871 white petrolatum Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP260796/92 | 1992-09-02 | ||
| JP26079692 | 1992-09-02 | ||
| JP12496493 | 1993-04-28 | ||
| JP124964/93 | 1993-04-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1086517A CN1086517A (zh) | 1994-05-11 |
| CN1039010C true CN1039010C (zh) | 1998-07-08 |
Family
ID=26461524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93116801A Expired - Fee Related CN1039010C (zh) | 1992-09-02 | 1993-09-02 | 噁二唑基取代的二氮杂萘衍生物、其中间体、其制法及其药物组合物和其在制药中的应用 |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US5367078A (OSRAM) |
| EP (1) | EP0588500B1 (OSRAM) |
| KR (1) | KR0157068B1 (OSRAM) |
| CN (1) | CN1039010C (OSRAM) |
| AT (1) | ATE172974T1 (OSRAM) |
| AU (1) | AU664912B2 (OSRAM) |
| CA (1) | CA2104267A1 (OSRAM) |
| CZ (1) | CZ180793A3 (OSRAM) |
| DE (1) | DE69321915T2 (OSRAM) |
| DK (1) | DK0588500T3 (OSRAM) |
| ES (1) | ES2124771T3 (OSRAM) |
| FI (1) | FI102899B1 (OSRAM) |
| HU (1) | HUT65324A (OSRAM) |
| IL (1) | IL106728A (OSRAM) |
| MX (1) | MX9305300A (OSRAM) |
| NO (1) | NO301011B1 (OSRAM) |
| PH (1) | PH30251A (OSRAM) |
| PL (1) | PL174330B1 (OSRAM) |
| RU (1) | RU2107686C1 (OSRAM) |
| SG (1) | SG81849A1 (OSRAM) |
| TW (1) | TW227562B (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9711257D0 (en) | 1997-05-30 | 1997-07-30 | Smithkline Beecham Plc | Novel compounds |
| TW486479B (en) * | 1997-07-15 | 2002-05-11 | Dainippon Pharmaceutical Co | 5-substituted-3-oxadiazolyl-1,6-naphthyridin-2(1H)-one derivatives |
| TWI262919B (en) * | 1999-10-25 | 2006-10-01 | Yamanouchi Pharma Co Ltd | Naphthyridine derivative |
| TWI298068B (en) * | 2000-06-21 | 2008-06-21 | Dainippon Sumitomo Pharma Co | Pharmaceutical composition for schizophrenia |
| JP4049297B2 (ja) | 2001-06-11 | 2008-02-20 | 株式会社ルネサステクノロジ | 半導体記憶装置 |
| AU2003249531A1 (en) * | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Azaisoquinoline derivatives as matrix metalloproteinase inhibitors |
| US20250002488A1 (en) * | 2021-10-12 | 2025-01-02 | Brown University | Glioblastoma Multiforme Treatments |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3555034A (en) * | 1968-06-18 | 1971-01-12 | American Home Prod | Certain 5,6,7,8-tetrahydro-1,6-naphthyridin-2-ol esters |
| JPS579780A (en) * | 1980-06-21 | 1982-01-19 | Otsuka Pharmaceut Co Ltd | Carbostyril derivative |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3535928A1 (de) * | 1985-10-04 | 1987-04-09 | Schering Ag | Tetrahydro-(beta)-carboline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| JPH08209780A (ja) * | 1995-02-06 | 1996-08-13 | Aisin Seiki Co Ltd | 便座装置 |
-
1993
- 1993-08-12 AU AU44587/93A patent/AU664912B2/en not_active Ceased
- 1993-08-17 CA CA002104267A patent/CA2104267A1/en not_active Abandoned
- 1993-08-18 AT AT93306510T patent/ATE172974T1/de not_active IP Right Cessation
- 1993-08-18 SG SG9600733A patent/SG81849A1/en unknown
- 1993-08-18 DK DK93306510T patent/DK0588500T3/da active
- 1993-08-18 EP EP93306510A patent/EP0588500B1/en not_active Expired - Lifetime
- 1993-08-18 DE DE69321915T patent/DE69321915T2/de not_active Expired - Fee Related
- 1993-08-18 ES ES93306510T patent/ES2124771T3/es not_active Expired - Lifetime
- 1993-08-18 IL IL10672893A patent/IL106728A/xx not_active IP Right Cessation
- 1993-08-19 PH PH46714A patent/PH30251A/en unknown
- 1993-08-24 TW TW082106850A patent/TW227562B/zh active
- 1993-08-27 US US08/112,660 patent/US5367078A/en not_active Expired - Fee Related
- 1993-08-31 MX MX9305300A patent/MX9305300A/es not_active IP Right Cessation
- 1993-09-01 RU RU93050211A patent/RU2107686C1/ru active
- 1993-09-01 NO NO933115A patent/NO301011B1/no not_active IP Right Cessation
- 1993-09-01 HU HU9302468A patent/HUT65324A/hu unknown
- 1993-09-01 FI FI933815A patent/FI102899B1/fi active
- 1993-09-01 CZ CZ931807A patent/CZ180793A3/cs unknown
- 1993-09-02 CN CN93116801A patent/CN1039010C/zh not_active Expired - Fee Related
- 1993-09-02 PL PL93300276A patent/PL174330B1/pl unknown
- 1993-09-02 KR KR1019930017471A patent/KR0157068B1/ko not_active Expired - Fee Related
-
1994
- 1994-06-16 US US08/260,800 patent/US5424433A/en not_active Expired - Fee Related
- 1994-06-16 US US08/260,835 patent/US5424434A/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3555034A (en) * | 1968-06-18 | 1971-01-12 | American Home Prod | Certain 5,6,7,8-tetrahydro-1,6-naphthyridin-2-ol esters |
| JPS579780A (en) * | 1980-06-21 | 1982-01-19 | Otsuka Pharmaceut Co Ltd | Carbostyril derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| IL106728A (en) | 1997-02-18 |
| PL174330B1 (pl) | 1998-07-31 |
| AU4458793A (en) | 1994-03-10 |
| CA2104267A1 (en) | 1994-03-03 |
| FI102899B (fi) | 1999-03-15 |
| ES2124771T3 (es) | 1999-02-16 |
| KR940007030A (ko) | 1994-04-26 |
| NO933115L (no) | 1994-03-03 |
| CN1086517A (zh) | 1994-05-11 |
| DE69321915T2 (de) | 1999-03-25 |
| ATE172974T1 (de) | 1998-11-15 |
| FI933815A0 (fi) | 1993-09-01 |
| RU2107686C1 (ru) | 1998-03-27 |
| DE69321915D1 (de) | 1998-12-10 |
| PH30251A (en) | 1997-02-05 |
| EP0588500A3 (en) | 1994-06-15 |
| SG81849A1 (en) | 2001-07-24 |
| US5424433A (en) | 1995-06-13 |
| FI102899B1 (fi) | 1999-03-15 |
| CZ180793A3 (en) | 1994-08-17 |
| PL300276A1 (en) | 1994-04-18 |
| HUT65324A (en) | 1994-05-02 |
| AU664912B2 (en) | 1995-12-07 |
| FI933815L (fi) | 1994-03-03 |
| US5424434A (en) | 1995-06-13 |
| EP0588500A2 (en) | 1994-03-23 |
| IL106728A0 (en) | 1993-12-08 |
| EP0588500B1 (en) | 1998-11-04 |
| KR0157068B1 (ko) | 1998-11-16 |
| TW227562B (OSRAM) | 1994-08-01 |
| DK0588500T3 (da) | 1999-07-19 |
| NO933115D0 (no) | 1993-09-01 |
| NO301011B1 (no) | 1997-09-01 |
| MX9305300A (es) | 1995-01-31 |
| US5367078A (en) | 1994-11-22 |
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| C19 | Lapse of patent right due to non-payment of the annual fee | ||
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