IE39263L - Naphthyridine derivatives - Google Patents
Naphthyridine derivativesInfo
- Publication number
- IE39263L IE39263L IE741012A IE101274A IE39263L IE 39263 L IE39263 L IE 39263L IE 741012 A IE741012 A IE 741012A IE 101274 A IE101274 A IE 101274A IE 39263 L IE39263 L IE 39263L
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- alkyl
- reaction
- prepared
- naphthyridine
- Prior art date
Links
- 150000005054 naphthyridines Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 abstract 1
- WLEQWVIWIDRMKX-UHFFFAOYSA-N 7-methoxy-1,8-naphthyridin-2-amine Chemical compound C1=CC(N)=NC2=NC(OC)=CC=C21 WLEQWVIWIDRMKX-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 229940125681 anticonvulsant agent Drugs 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 150000003949 imides Chemical class 0.000 abstract 1
- VIIPRKFEGDDHCU-UHFFFAOYSA-N n-(7-chloro-1,8-naphthyridin-2-yl)acetamide Chemical compound C1=CC(Cl)=NC2=NC(NC(=O)C)=CC=C21 VIIPRKFEGDDHCU-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/24—Oxygen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
Abstract
1417935 Naphthyridine derivatives RHONEPOULENC SA 13 May 1974 [15 May 1973 14 March 1974 (2)] 21081/74 Heading C2C Novel compounds I (in which one symbol X is =N-and the others are all -CY=; Y is H, halo, 1-4 C alkyl or alkoxy, CN or NO 2 ; A is =CH- and A 1 is =CH- or =N- or A is =N- and A 1 is =N-; Z is H, halo, 1-4 C alkyl or alkoxy or NO 2 ; m is 0 or 1-4; and (i) n is O or R is H, 1-4 C alkyl, 2-4 C alkenyl or alkynyl, 1-4 C hydroxyalkyl or phenyl or (ii) n is 1 and R is 1-4 C alkyl or hydroxyalkyl or phenyl) and acid addition salts thereof are prepared by (i) reaction of a piperazine II with a naphthyridine III or an alkali metal derivative thereof; (ii) reaction of a piperazine VIII with a mixed carbonate IX (in which Ar is phenyl which may be substituted by 1-4 C alkyl or NO 2 ) or (iii) oxidation of a compound I in which n is 0 to give a compound in which n is 1. Compounds III may be prepared by reaction of a compound V with a compound VI to give a compound VII cyclization of the compound VII to give an imide IV which is then partially reduced. Compounds VIII in which n is 1 may be prepared by oxidation of those in which n is 0. Compounds IX may be prepared by reaction of a chloroformate CICOOAr with a compound III. 2 - Amino - 7 - methoxy - 1,8 - naphthyridine is prepared by reaction of sodium methoxide with 2 - acetamido - 7 - chloro - 1,8 - naphthyridine. Pharmaceutical compositions useful as anticonvulsants and tranquillizers comprise a compound I or a suitable salt thereof in combination with a carrier or diluent.
[GB1417935A]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7317516A FR2229400A1 (en) | 1973-05-15 | 1973-05-15 | 2-(Naphthyridin-2-yl)-isoindolin-1-one derivs - contg. 3-(piperazin-1-yl-carbonyloxy) gp., used as tranquillisers and antidepressants |
| FR7408728A FR2286642A2 (en) | 1974-03-14 | 1974-03-14 | 2-(Naphthyridin-2-yl)-isoindolin-1-one derivs - contg. 3-(piperazin-1-yl-carbonyloxy) gp., used as tranquillisers and antidepressants |
| FR7408730A FR2263752A1 (en) | 1974-03-14 | 1974-03-14 | 1,8-Naphthyridine derivs - tranquillizers and anti-convulsants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE39263L true IE39263L (en) | 1974-11-15 |
| IE39263B1 IE39263B1 (en) | 1978-08-30 |
Family
ID=27250114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1012/74A IE39263B1 (en) | 1973-05-15 | 1974-05-13 | Naphthyridine derivatives |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5758345B2 (en) |
| AR (2) | AR209421A1 (en) |
| AT (1) | AT336030B (en) |
| CH (2) | CH592662A5 (en) |
| CS (1) | CS191881B2 (en) |
| DD (1) | DD111078A5 (en) |
| DE (1) | DE2423650A1 (en) |
| DK (1) | DK136819B (en) |
| ES (2) | ES426336A1 (en) |
| FI (1) | FI55659C (en) |
| GB (1) | GB1417935A (en) |
| HU (1) | HU169609B (en) |
| IE (1) | IE39263B1 (en) |
| IL (1) | IL44815A (en) |
| LU (1) | LU70071A1 (en) |
| NL (1) | NL7406194A (en) |
| NO (1) | NO140012C (en) |
| OA (1) | OA04700A (en) |
| PH (1) | PH11400A (en) |
| PL (1) | PL90061B1 (en) |
| SE (1) | SE410857B (en) |
| SU (2) | SU583757A3 (en) |
| YU (2) | YU133674A (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS537455B1 (en) * | 1971-02-01 | 1978-03-17 | ||
| FR2324305A2 (en) * | 1975-09-22 | 1977-04-15 | Rhone Poulenc Ind | NEW DERIVATIVES OF ISOINDOLINE, THEIR PREPARATION AND THE COMPOSITIONS CONTAINING THEM |
| FR2322600A1 (en) * | 1975-09-04 | 1977-04-01 | Rhone Poulenc Ind | Pyrrolidinone deriirrivs as tranquillizers - 1-Heterocyclyl-5(1-piperazinyl-carbonyloxy)-2(5H)-pyrrolidinone derivs prepd. from 5-aryloxycarbonyloxy cpds. and piperazine (OE060576) |
| AR208414A1 (en) * | 1974-11-07 | 1976-12-27 | Rhone Poulenc Ind | PROCEDURE TO OBTAIN NEW DERIVATIVES OF ((ACIL-4PIPERAZINIL-1) CARBONYLOXI-5 PYRROLINONE-2) |
| OA05287A (en) * | 1975-04-07 | 1981-02-28 | Rhone Poulenc Ind | New heterocyclic compounds and their preparation. |
| JPS5546257A (en) * | 1978-09-27 | 1980-03-31 | Hitachi Cable | Flame retardant cable |
| JPS5546256A (en) * | 1978-09-27 | 1980-03-31 | Hitachi Cable | Flame retardant insulated wire |
| JPS63191981U (en) * | 1987-05-30 | 1988-12-09 | ||
| SK282252B6 (en) * | 1995-01-11 | 2001-12-03 | Samjin Pharmaceutical Co., Ltd. | New piperazine derivatives and pharmaceutical composition containing the same |
| EP0850222B1 (en) * | 1996-06-29 | 2003-05-28 | Samjin Pharmaceutical Co., Ltd. | Piperazine derivatives and process for the preparation thereof |
-
1974
- 1974-04-29 OA OA55189A patent/OA04700A/en unknown
- 1974-04-30 PH PH15794A patent/PH11400A/en unknown
- 1974-05-08 NL NL7406194A patent/NL7406194A/xx not_active Application Discontinuation
- 1974-05-13 GB GB2108174A patent/GB1417935A/en not_active Expired
- 1974-05-13 HU HURO780A patent/HU169609B/hu unknown
- 1974-05-13 IL IL44815A patent/IL44815A/en unknown
- 1974-05-13 JP JP49052378A patent/JPS5758345B2/ja not_active Expired
- 1974-05-13 IE IE1012/74A patent/IE39263B1/en unknown
- 1974-05-14 CH CH659574A patent/CH592662A5/xx not_active IP Right Cessation
- 1974-05-14 ES ES426336A patent/ES426336A1/en not_active Expired
- 1974-05-14 CH CH53477A patent/CH592663A5/xx not_active IP Right Cessation
- 1974-05-14 NO NO741744A patent/NO140012C/en unknown
- 1974-05-14 ES ES426335A patent/ES426335A1/en not_active Expired
- 1974-05-14 DD DD178499A patent/DD111078A5/xx unknown
- 1974-05-14 LU LU70071A patent/LU70071A1/xx unknown
- 1974-05-14 DK DK263374AA patent/DK136819B/en not_active IP Right Cessation
- 1974-05-14 SU SU7402026597A patent/SU583757A3/en active
- 1974-05-14 SE SE7406452A patent/SE410857B/en not_active IP Right Cessation
- 1974-05-15 CS CS743472A patent/CS191881B2/en unknown
- 1974-05-15 DE DE2423650A patent/DE2423650A1/en not_active Withdrawn
- 1974-05-15 AT AT400874A patent/AT336030B/en not_active IP Right Cessation
- 1974-05-15 FI FI1498/74A patent/FI55659C/en active
- 1974-05-15 YU YU01336/74A patent/YU133674A/en unknown
- 1974-05-15 PL PL1974171103A patent/PL90061B1/en unknown
- 1974-05-15 AR AR253755A patent/AR209421A1/en active
-
1975
- 1975-01-29 AR AR257458A patent/AR210851A1/en active
- 1975-03-18 SU SU752112823A patent/SU589916A3/en active
-
1981
- 1981-12-08 YU YU02877/81A patent/YU287781A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7406194A (en) | 1974-11-19 |
| YU133674A (en) | 1983-01-21 |
| JPS5040593A (en) | 1975-04-14 |
| ES426336A1 (en) | 1976-07-01 |
| PH11400A (en) | 1977-12-14 |
| HU169609B (en) | 1976-12-28 |
| LU70071A1 (en) | 1975-02-24 |
| SE410857B (en) | 1979-11-12 |
| AT336030B (en) | 1977-04-12 |
| ATA400874A (en) | 1976-08-15 |
| GB1417935A (en) | 1975-12-17 |
| PL90061B1 (en) | 1976-12-31 |
| DK136819C (en) | 1978-05-16 |
| FI55659C (en) | 1979-09-10 |
| DE2423650A1 (en) | 1974-12-05 |
| SU583757A3 (en) | 1977-12-05 |
| ES426335A1 (en) | 1976-09-01 |
| FI55659B (en) | 1979-05-31 |
| SU589916A3 (en) | 1978-01-25 |
| DK136819B (en) | 1977-11-28 |
| IL44815A0 (en) | 1975-02-10 |
| NO741744L (en) | 1974-11-18 |
| IE39263B1 (en) | 1978-08-30 |
| NO140012C (en) | 1979-06-20 |
| CH592662A5 (en) | 1977-10-31 |
| IL44815A (en) | 1977-12-30 |
| AR209421A1 (en) | 1977-04-29 |
| NO140012B (en) | 1979-03-12 |
| OA04700A (en) | 1980-07-31 |
| AU6888074A (en) | 1975-11-13 |
| AR210851A1 (en) | 1977-09-30 |
| CH592663A5 (en) | 1977-10-31 |
| YU287781A (en) | 1983-01-21 |
| JPS5758345B2 (en) | 1982-12-09 |
| CS191881B2 (en) | 1979-07-31 |
| DD111078A5 (en) | 1975-01-20 |
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