KR840000521A - 3-메틸플라본-8-카르복실산 에스테르류의 제조방법 - Google Patents
3-메틸플라본-8-카르복실산 에스테르류의 제조방법 Download PDFInfo
- Publication number
- KR840000521A KR840000521A KR1019820003175A KR820003175A KR840000521A KR 840000521 A KR840000521 A KR 840000521A KR 1019820003175 A KR1019820003175 A KR 1019820003175A KR 820003175 A KR820003175 A KR 820003175A KR 840000521 A KR840000521 A KR 840000521A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- group
- methylflavone
- carbon atoms
- hydrogen atom
- Prior art date
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- KMMBBZOSQNLLMN-UHFFFAOYSA-N 3-methylflavone-8-carboxylic acid Chemical class O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 KMMBBZOSQNLLMN-UHFFFAOYSA-N 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 150000002212 flavone derivatives Chemical class 0.000 claims 3
- -1 3-methylflavone-8-carboxylic acid halide Chemical class 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000001414 amino alcohols Chemical class 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229930003944 flavone Natural products 0.000 claims 1
- 235000011949 flavones Nutrition 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- UOIWRLPZDGOIQS-UHFFFAOYSA-N oxiran-2-ylmethyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OCC1CO1 UOIWRLPZDGOIQS-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003053 piperidines Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- A61P23/02—Local anaesthetics
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/12—Oxygen atoms acylated by aromatic or heteroaromatic carboxylic acids, e.g. cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Anesthesiology (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (8)
- 하기식 (Ⅲ)의 3-메틸플라본-8-카르복실산 할라이드를 일반식 ZOH의 아미노알코올과 축합시킴을 특징으로 하는 하기식 (Ⅰ)의 3-메틸플라본-8-카르복실산 에스테르 또는 약학적으로 허용되는 그의 염의 제조방법.여기서, Z는 N-메틸피페리딜, 트로필 또는 퀴뉴클리딜기 또는 일반식(Ⅱ)의 기를 나타내고, n은 0 또는 1이고, R은 수소원자, 탄소원자수 1~4의 알킬기 또는 페닐기를 나타내고, R1은 수소원자 또는 탄소원자수 1~4의 알킬기를 나타내고, R2는 수소원지 또는 히드록시기를 나타내고, 또는 R, R1및 R2는 이들이 연결되어 있는 탄소원자들과 함께 탄소원자수 4~6의 시클로 환을 이루며, R3는 수소원자 또는 탄소원자수 1~4의 알킬기를 나타내며, X는 할로겐 원자를 나타낸다.
- 제 1 항에 있어서, X가 염소원자를 나타냄을 특징으로 하는 방법.
- 제 1 또는 2 항에 있어서, 140℃~100℃의 온도에서 용매 부재하 아미노 알코올 및 과량의 플라본 유도체를 가열시킴으로써 반응이 수행됨을 특징으로 하는 방법.
- 제 1 또는 2 항에 있어서, 0℃ 내지 용매의 환류 온도에서 용매 존재하, 아미노 알코올을 동량의 플라본 유도체와 반응시킴으로써 반응이 수행됨을 특징으로 하는 방법.
- 제 4 항에 있어서, 산 결합제 존재하 반응이 수행됨을 특징으로 하는 방법.
- 하기식 (Ⅳ)의 화합물을 촉매 존재하 2,3-에폭시프로필-3-메틸플라본-8-카르복실레이트와 반응시킴을 특징으로 하는 하기식 (Ⅰ)의 3-메틸플라본-8-카르복실산 에스테르의 제조방법.여기서, Z는 상기식 (Ⅱ)의 기를 나타내고 n은 1이고, R 및 R1은 수소원자를 나타내고, R2는 히드록시기를 나타내고, R3는 수소원자 또는 탄소원자수 1~4의 알킬기를 나타낸다.
- 제 6 항에 있어서, 촉매가 트리에틸아민임을 특징으로 하는 방법.
- 제 7 항에 있어서, 동몰비의 플라본 및 피페리딘 유도체를 사용하여 20~80℃에서, 반응이 용매 내에서 수행됨을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8122158 | 1981-07-17 | ||
| GB8122158 | 1981-07-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840000521A true KR840000521A (ko) | 1984-02-25 |
| KR870000275B1 KR870000275B1 (ko) | 1987-02-23 |
Family
ID=10523330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8203175A KR870000275B1 (ko) | 1981-07-17 | 1982-07-16 | 3-메틸플라본-8-카르복실산 에스테르류의 제조방법 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4550115A (ko) |
| EP (1) | EP0072620B1 (ko) |
| JP (1) | JPS5835185A (ko) |
| KR (1) | KR870000275B1 (ko) |
| AR (1) | AR231543A1 (ko) |
| AT (1) | ATE16806T1 (ko) |
| AU (1) | AU553322B2 (ko) |
| CA (1) | CA1221969A (ko) |
| DE (1) | DE3267782D1 (ko) |
| DK (1) | DK160498C (ko) |
| ES (1) | ES513993A0 (ko) |
| FI (1) | FI73677C (ko) |
| GB (1) | GB2104507B (ko) |
| GR (1) | GR81300B (ko) |
| HU (1) | HU189601B (ko) |
| IE (1) | IE53525B1 (ko) |
| IL (1) | IL66187A0 (ko) |
| IT (1) | IT1198389B (ko) |
| NO (1) | NO157330C (ko) |
| NZ (1) | NZ200981A (ko) |
| PH (1) | PH18001A (ko) |
| PT (1) | PT75230B (ko) |
| SG (1) | SG77784G (ko) |
| YU (2) | YU136682A (ko) |
| ZA (1) | ZA824335B (ko) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58225083A (ja) * | 1982-06-23 | 1983-12-27 | Nippon Shinyaku Co Ltd | メチルフラボン誘導体 |
| FR2531083B1 (fr) * | 1982-06-29 | 1986-11-28 | Sandoz Sa | Nouveaux derives de la piperidine, leur preparation et leur utilisation comme medicaments |
| IT1229856B (it) * | 1989-04-20 | 1991-09-13 | Recordati Chem Pharm | Compresse a rilascio controllato contenenti flavossato. |
| IT1254469B (it) * | 1992-02-25 | 1995-09-25 | Recordati Chem Pharm | Derivati benzopiranici e benzotiopiranici |
| EP0558245A1 (en) | 1992-02-25 | 1993-09-01 | RECORDATI S.A. CHEMICAL and PHARMACEUTICAL COMPANY | Heterobicyclic compounds as antagogists of alpha-1 adrenergic and SHT1A receptors |
| US5474994A (en) * | 1992-05-26 | 1995-12-12 | Recordati S.A., Chemical And Pharmaceutical Company | Bicyclic heterocyclic derivatives having α1 -adrenergic and 5HT1A |
| US5605896A (en) * | 1992-02-25 | 1997-02-25 | Recordati S.A., Chemical And Pharmaceutical Company | Bicyclic heterocyclic derivatives having α1 adrenergic and 5HT1A activities |
| IT1258315B (it) * | 1992-04-10 | 1996-02-22 | Recordati Chem Pharm | Derivati del flavone |
| US6087366A (en) * | 1996-03-07 | 2000-07-11 | The Trustees Of Columbia University In The City Of New York | Use of flavopiridol or a pharmaceutically acceptable salt thereof for inhibiting cell damage or cell death |
| ATE386738T1 (de) | 2002-12-23 | 2008-03-15 | Ranbaxy Lab Ltd | Flavaxat-derivate als muscarin-rezeptor antagonisten |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2921070A (en) * | 1957-11-05 | 1960-01-12 | Recordati Lab Farmacologico S | Basic esters of 3-methylflavone-8-carboxylic acid |
| US4217351A (en) * | 1976-08-04 | 1980-08-12 | Abbott Laboratories | Benzopyrano quinuclidines useful as antiglaucoma agents |
-
1982
- 1982-06-16 NZ NZ200981A patent/NZ200981A/en unknown
- 1982-06-18 ZA ZA824335A patent/ZA824335B/xx unknown
- 1982-06-18 GB GB08217744A patent/GB2104507B/en not_active Expired
- 1982-06-23 YU YU01366/82A patent/YU136682A/xx unknown
- 1982-06-24 NO NO822127A patent/NO157330C/no unknown
- 1982-06-29 AR AR289821A patent/AR231543A1/es active
- 1982-07-01 IL IL66187A patent/IL66187A0/xx not_active IP Right Cessation
- 1982-07-05 CA CA000406549A patent/CA1221969A/en not_active Expired
- 1982-07-06 DK DK301982A patent/DK160498C/da not_active IP Right Cessation
- 1982-07-07 IT IT22274/82A patent/IT1198389B/it active
- 1982-07-09 EP EP82303634A patent/EP0072620B1/en not_active Expired
- 1982-07-09 AT AT82303634T patent/ATE16806T1/de not_active IP Right Cessation
- 1982-07-09 DE DE8282303634T patent/DE3267782D1/de not_active Expired
- 1982-07-12 IE IE1678/82A patent/IE53525B1/en not_active IP Right Cessation
- 1982-07-12 PT PT75230A patent/PT75230B/pt not_active IP Right Cessation
- 1982-07-12 PH PH27559A patent/PH18001A/en unknown
- 1982-07-12 US US06/397,196 patent/US4550115A/en not_active Expired - Fee Related
- 1982-07-13 FI FI822493A patent/FI73677C/fi not_active IP Right Cessation
- 1982-07-14 JP JP57123732A patent/JPS5835185A/ja active Granted
- 1982-07-15 ES ES513993A patent/ES513993A0/es active Granted
- 1982-07-15 GR GR68773A patent/GR81300B/el unknown
- 1982-07-16 AU AU86098/82A patent/AU553322B2/en not_active Ceased
- 1982-07-16 HU HU822322A patent/HU189601B/hu not_active IP Right Cessation
- 1982-07-16 KR KR8203175A patent/KR870000275B1/ko active
-
1984
- 1984-07-16 YU YU01251/84A patent/YU125184A/xx unknown
- 1984-11-02 SG SG777/84A patent/SG77784G/en unknown
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