CZ180793A3 - Novel 3-oxadiazolyl-1,6-naphthyridine derivatives - Google Patents
Novel 3-oxadiazolyl-1,6-naphthyridine derivatives Download PDFInfo
- Publication number
- CZ180793A3 CZ180793A3 CZ931807A CZ180793A CZ180793A3 CZ 180793 A3 CZ180793 A3 CZ 180793A3 CZ 931807 A CZ931807 A CZ 931807A CZ 180793 A CZ180793 A CZ 180793A CZ 180793 A3 CZ180793 A3 CZ 180793A3
- Authority
- CZ
- Czechia
- Prior art keywords
- compound
- group
- tetrahydro
- benzyl
- pharmaceutically acceptable
- Prior art date
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- USGLLKJABJGFAZ-UHFFFAOYSA-N 4-(1,6-naphthyridin-3-yl)oxadiazole Chemical class O1N=NC(C=2C=C3C=NC=CC3=NC=2)=C1 USGLLKJABJGFAZ-UHFFFAOYSA-N 0.000 title description 2
- 239000002253 acid Substances 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
- 125000002252 acyl group Chemical group 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 139
- 238000000034 method Methods 0.000 claims description 40
- 238000002360 preparation method Methods 0.000 claims description 32
- -1 6-benzyl-3- (5-cyclopropyl-1,3,4-oxadiazol-2-yl) -5,6,7,8-tetrahydro-1,6-naphthyridine Chemical compound 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
- 238000006210 cyclodehydration reaction Methods 0.000 claims description 4
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- BZLLVTYOOJNQIF-UHFFFAOYSA-N (3e)-6-benzyl-3-(5-methoxy-1,3,4-oxadiazol-2(3h)-ylidene)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(3h)-one Chemical compound O1C(OC)=NN=C1C(C(N1)=O)=CC2=C1CCN(CC=1C=CC=CC=1)C2 BZLLVTYOOJNQIF-UHFFFAOYSA-N 0.000 claims 1
- VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical class C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 claims 1
- FPEAARFNXIWCTP-UHFFFAOYSA-N 5,6,7,8-tetrahydro-1,6-naphthyridine Chemical compound C1=CC=C2CNCCC2=N1 FPEAARFNXIWCTP-UHFFFAOYSA-N 0.000 claims 1
- BJJKPGRNERQNGU-UHFFFAOYSA-N 6-[(2-bromo-5-fluorophenyl)methyl]-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-1,5,7,8-tetrahydro-1,6-naphthyridin-2-one Chemical compound O1C(OC)=NN=C1C(C(N1)=O)=CC2=C1CCN(CC=1C(=CC=C(F)C=1)Br)C2 BJJKPGRNERQNGU-UHFFFAOYSA-N 0.000 claims 1
- KLHWCRYJKXJVNT-UHFFFAOYSA-N 6-[(2-bromophenyl)methyl]-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-1,5,7,8-tetrahydro-1,6-naphthyridin-2-one Chemical compound O1C(OC)=NN=C1C(C(N1)=O)=CC2=C1CCN(CC=1C(=CC=CC=1)Br)C2 KLHWCRYJKXJVNT-UHFFFAOYSA-N 0.000 claims 1
- OVPAORUHJLWTDO-UHFFFAOYSA-N 6-[(2-chloro-5-fluorophenyl)methyl]-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-1,5,7,8-tetrahydro-1,6-naphthyridin-2-one Chemical compound COc1nnc(o1)-c1cc2CN(Cc3cc(F)ccc3Cl)CCc2[nH]c1=O OVPAORUHJLWTDO-UHFFFAOYSA-N 0.000 claims 1
- ZJZRURJPCFAEDB-UHFFFAOYSA-N 6-[(2-chlorophenyl)methyl]-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-1,5,7,8-tetrahydro-1,6-naphthyridin-2-one Chemical compound O1C(OC)=NN=C1C(C(N1)=O)=CC2=C1CCN(CC=1C(=CC=CC=1)Cl)C2 ZJZRURJPCFAEDB-UHFFFAOYSA-N 0.000 claims 1
- GIPOJACPFFVFMJ-UHFFFAOYSA-N 6-[(4-chlorophenyl)methyl]-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-1,5,7,8-tetrahydro-1,6-naphthyridin-2-one Chemical compound O1C(OC)=NN=C1C(C(N1)=O)=CC2=C1CCN(CC=1C=CC(Cl)=CC=1)C2 GIPOJACPFFVFMJ-UHFFFAOYSA-N 0.000 claims 1
- JCXALDUUVYLQFY-UHFFFAOYSA-N 6-benzyl-3-(5-ethyl-1,3,4-oxadiazol-2-yl)-1,5,7,8-tetrahydro-1,6-naphthyridin-2-one Chemical compound O1C(CC)=NN=C1C(C(N1)=O)=CC2=C1CCN(CC=1C=CC=CC=1)C2 JCXALDUUVYLQFY-UHFFFAOYSA-N 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- OMFARWAPFVGOEC-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydro-1,6-naphthyridin-3-yl)oxadiazole Chemical class C1=C2CNCCC2=NC=C1C1=CON=N1 OMFARWAPFVGOEC-UHFFFAOYSA-N 0.000 abstract description 2
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- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
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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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26079692 | 1992-09-02 | ||
| JP12496493 | 1993-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ180793A3 true CZ180793A3 (en) | 1994-08-17 |
Family
ID=26461524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ931807A CZ180793A3 (en) | 1992-09-02 | 1993-09-01 | Novel 3-oxadiazolyl-1,6-naphthyridine derivatives |
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 |
Family Cites Families (4)
| 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 |
| 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
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 |
| CN1039010C (zh) | 1998-07-08 |
| 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 |
| 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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