FI71155C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 9-halogen-7-oxo-2,3-dihydro-7h-pyrido/1,2,3-de/ /1,4/bensoxazin-6-karboxylsyraderivat - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 9-halogen-7-oxo-2,3-dihydro-7h-pyrido/1,2,3-de/ /1,4/bensoxazin-6-karboxylsyraderivat Download PDFInfo
- Publication number
- FI71155C FI71155C FI812693A FI812693A FI71155C FI 71155 C FI71155 C FI 71155C FI 812693 A FI812693 A FI 812693A FI 812693 A FI812693 A FI 812693A FI 71155 C FI71155 C FI 71155C
- Authority
- FI
- Finland
- Prior art keywords
- dihydro
- oxo
- pyrido
- carboxylic acid
- methyl
- Prior art date
Links
- 230000001225 therapeutic effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 33
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- 238000000034 method Methods 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 10
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
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- 125000004429 atom Chemical group 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
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- 125000003277 amino group Chemical class 0.000 abstract description 2
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- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
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- 238000006722 reduction reaction Methods 0.000 description 3
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- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- YIFCWYUSYGFFMH-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedioic acid Chemical compound CCOC=C(C(O)=O)C(O)=O YIFCWYUSYGFFMH-UHFFFAOYSA-N 0.000 description 2
- QHXNXZWZWUJJEE-UHFFFAOYSA-N 3-chloro-2-fluoro-6-nitrophenol Chemical compound OC1=C(F)C(Cl)=CC=C1[N+]([O-])=O QHXNXZWZWUJJEE-UHFFFAOYSA-N 0.000 description 2
- OYJNFTPNBSNXQD-UHFFFAOYSA-N 7-chloro-8-fluoro-3-methyl-3,4-dihydro-2h-1,4-benzoxazine Chemical compound ClC1=CC=C2NC(C)COC2=C1F OYJNFTPNBSNXQD-UHFFFAOYSA-N 0.000 description 2
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- FHFYDNQZQSQIAI-UHFFFAOYSA-N pefloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C)CC1 FHFYDNQZQSQIAI-UHFFFAOYSA-N 0.000 description 2
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- 208000020029 respiratory tract infectious disease Diseases 0.000 description 2
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- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- 208000019206 urinary tract infection Diseases 0.000 description 2
- ARCACZWMYGILNI-UHFFFAOYSA-N 1,2,3-trifluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1F ARCACZWMYGILNI-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- RUBQQRMAWLSCCJ-UHFFFAOYSA-N 1,2-difluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1 RUBQQRMAWLSCCJ-UHFFFAOYSA-N 0.000 description 1
- JSEVUBOYVADSHX-UHFFFAOYSA-N 1,3-dichloro-2-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(F)=C1Cl JSEVUBOYVADSHX-UHFFFAOYSA-N 0.000 description 1
- ZJVPAAJHCJMGGL-UHFFFAOYSA-N 1-(2,3-difluoro-6-nitrophenoxy)propan-2-one Chemical compound CC(=O)COC1=C(F)C(F)=CC=C1[N+]([O-])=O ZJVPAAJHCJMGGL-UHFFFAOYSA-N 0.000 description 1
- XDHOZVQJAXHHAL-UHFFFAOYSA-N 1-(3-chloro-2-fluoro-6-nitrophenoxy)propan-2-one Chemical compound CC(=O)COC1=C(F)C(Cl)=CC=C1[N+]([O-])=O XDHOZVQJAXHHAL-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- KGFBMLJHIYBHHR-UHFFFAOYSA-N 2-(2-bromoethoxy)-3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1OCCBr KGFBMLJHIYBHHR-UHFFFAOYSA-N 0.000 description 1
- 125000006016 2-bromoethoxy group Chemical group 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- UZHLWFXRBVODHQ-UHFFFAOYSA-N 4-ethyl-5-oxo-2-piperazin-1-yl-8h-pyrido[2,3-d]pyrimidine-6-carboxylic acid Chemical compound N=1C=2NC=C(C(O)=O)C(=O)C=2C(CC)=NC=1N1CCNCC1 UZHLWFXRBVODHQ-UHFFFAOYSA-N 0.000 description 1
- BVHSAZFNVBBGNX-UHFFFAOYSA-N 7,8-difluoro-3-methyl-3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC(F)=C(F)C2=C1NC(C)CO2 BVHSAZFNVBBGNX-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
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- 125000004043 oxo group Chemical group O=* 0.000 description 1
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
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- CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55121540A JPS5746986A (en) | 1980-09-02 | 1980-09-02 | Pyrido(1,2,3-de)(1,4)benzoxazine derivative |
| JP12154080 | 1980-09-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI812693L FI812693L (fi) | 1982-03-03 |
| FI71155B FI71155B (fi) | 1986-08-14 |
| FI71155C true FI71155C (fi) | 1986-11-24 |
Family
ID=14813767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI812693A FI71155C (fi) | 1980-09-02 | 1981-09-01 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 9-halogen-7-oxo-2,3-dihydro-7h-pyrido/1,2,3-de/ /1,4/bensoxazin-6-karboxylsyraderivat |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4382892A (en, 2012) |
| EP (1) | EP0047005B1 (en, 2012) |
| JP (1) | JPS5746986A (en, 2012) |
| KR (1) | KR840002141B1 (en, 2012) |
| AT (1) | ATE10282T1 (en, 2012) |
| AU (1) | AU529263B2 (en, 2012) |
| CA (1) | CA1167840A (en, 2012) |
| DE (1) | DE3167216D1 (en, 2012) |
| DK (2) | DK158267C (en, 2012) |
| ES (1) | ES8301977A1 (en, 2012) |
| FI (1) | FI71155C (en, 2012) |
| GR (1) | GR74637B (en, 2012) |
| HK (1) | HK82186A (en, 2012) |
| IL (1) | IL63613A (en, 2012) |
| IN (1) | IN155680B (en, 2012) |
| MY (1) | MY8600712A (en, 2012) |
| NO (1) | NO158507C (en, 2012) |
| NZ (1) | NZ198224A (en, 2012) |
| PH (1) | PH18276A (en, 2012) |
| YU (2) | YU42422B (en, 2012) |
| ZA (1) | ZA815604B (en, 2012) |
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| JPS54138582A (en) | 1978-04-19 | 1979-10-27 | Kyorin Seiyaku Kk | Substituted quinolinecarboxylic acid |
| JPS5845426B2 (ja) * | 1978-09-29 | 1983-10-08 | 杏林製薬株式会社 | 置換キノリンカルボン酸誘導体 |
-
1980
- 1980-09-02 JP JP55121540A patent/JPS5746986A/ja active Granted
-
1981
- 1981-08-12 PH PH26040A patent/PH18276A/en unknown
- 1981-08-13 ZA ZA815604A patent/ZA815604B/xx unknown
- 1981-08-19 IL IL63613A patent/IL63613A/xx not_active IP Right Cessation
- 1981-08-28 DE DE8181106747T patent/DE3167216D1/de not_active Expired
- 1981-08-28 AT AT81106747T patent/ATE10282T1/de not_active IP Right Cessation
- 1981-08-28 EP EP81106747A patent/EP0047005B1/en not_active Expired
- 1981-08-31 KR KR1019810003207A patent/KR840002141B1/ko not_active Expired
- 1981-09-01 FI FI812693A patent/FI71155C/fi not_active IP Right Cessation
- 1981-09-01 ES ES505116A patent/ES8301977A1/es not_active Expired
- 1981-09-01 YU YU2109/81A patent/YU42422B/xx unknown
- 1981-09-01 NZ NZ198224A patent/NZ198224A/en unknown
- 1981-09-01 NO NO812956A patent/NO158507C/no unknown
- 1981-09-02 CA CA000385046A patent/CA1167840A/en not_active Expired
- 1981-09-02 AU AU74878/81A patent/AU529263B2/en not_active Expired
- 1981-09-02 DK DK388981A patent/DK158267C/da not_active IP Right Cessation
- 1981-09-02 US US06/298,816 patent/US4382892A/en not_active Expired - Lifetime
- 1981-09-02 IN IN985/CAL/81A patent/IN155680B/en unknown
- 1981-09-02 GR GR65931A patent/GR74637B/el unknown
-
1986
- 1986-10-30 HK HK821/86A patent/HK82186A/en not_active IP Right Cessation
- 1986-12-30 MY MY712/86A patent/MY8600712A/xx unknown
-
1988
- 1988-04-14 YU YU74788A patent/YU47193B/sh unknown
- 1988-04-14 DK DK204488A patent/DK204488A/da not_active Application Discontinuation
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Owner name: DAIICHI PHARMACEUTICAL CO.,_LTD. |