KR890008072A - 벤조사이클로헵텐 유도체 - Google Patents
벤조사이클로헵텐 유도체 Download PDFInfo
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- KR890008072A KR890008072A KR1019880014556A KR880014556A KR890008072A KR 890008072 A KR890008072 A KR 890008072A KR 1019880014556 A KR1019880014556 A KR 1019880014556A KR 880014556 A KR880014556 A KR 880014556A KR 890008072 A KR890008072 A KR 890008072A
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- Prior art keywords
- propenyl
- tetrahydro
- benzocyclohepten
- benzoate
- compound
- Prior art date
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- ZVCPCZRXWGOICC-UHFFFAOYSA-N 1h-benzo[7]annulene Chemical class C1=CC=CC=C2CC=CC=C21 ZVCPCZRXWGOICC-UHFFFAOYSA-N 0.000 title 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 33
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 27
- -1 lower-alkoxy Chemical group 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 239000005711 Benzoic acid Substances 0.000 claims 8
- 235000010233 benzoic acid Nutrition 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 150000001735 carboxylic acids Chemical class 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 229910052736 halogen Chemical group 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 102000011782 Keratins Human genes 0.000 claims 1
- 108010076876 Keratins Proteins 0.000 claims 1
- 206010039792 Seborrhoea Diseases 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 230000003266 anti-allergic effect Effects 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 150000002148 esters Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 208000008742 seborrheic dermatitis Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
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- C07—ORGANIC CHEMISTRY
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/618—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety having unsaturation outside the six-membered aromatic ring
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/19—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups having unsaturation outside the aromatic ring
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- 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]
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- 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
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- C07C33/05—Alcohols containing rings other than six-membered aromatic rings
- C07C33/16—Alcohols containing rings other than six-membered aromatic rings containing rings with more than six ring members
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/457—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing halogen
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
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- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/74—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen having unsaturation outside the aromatic rings
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- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/32—All rings being cycloaliphatic the ring system containing at least eleven carbon atoms
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- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
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- Immunology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
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- Organic Insulating Materials (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
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Description
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Claims (20)
- 하기 일반식 (I)의 화합물 및 일반식 (I)의 카복실산의 생리학적으로 허용되는 염상기식에서 R¹은 하이드록시, 저급-알콕시, 아미노, 모노 또는 디 - 저급 - 알킬아미노이고 : R²은 수소, 알킬, 알콕시 또는 할로겐이며 : R3,R4,R5,R6,R11및 R12는 각각 독립적으로 수소 또는 저급 - 알킬이고 : R³ 및 R5가 함께는 메틸렌 또는 하이드록시-메틸렌 그룹이며, R7,R8,R9및 R10은 수소 또는 저급 알킬이고 : R11및 R12가 함께는 옥소그룹 또는 스피로-사이클로-저급 알킬이거나, 또는 R11은 수소이며, R12는 하이드록시 또는 아세톡시이고, 잔기 R13및 R14중 하나는 수소이며, 다른 하나는 저급-알킬 또는 트리플루오르메틸이다
- 제 1 항에 있어서, R¹이 하이드록시, 저급 - 알콕시, 아미노, 모노-또는 디 - 저급 -알킬아미노이고 : R²는 수소, 알킬, 알콕시 또는 할로겐이며 : R3,R4,R5,R6,R11및 R12는 각각 독립적으로 수소 또는 저급 - 알킬이고 : R³ 및 R⁴가 함께는 메틸렌 그룹이며 : R7,R8,R9및 R10은 수소 또는 저급 - 일킬이고 : R11및 Rg함께는 옥소 그룹이거나, 또는 R11은 수소이며, R12는 하이드록시이고 : 잔기 R13및 R14중 하나는 수소이며, 다른 하나는 저급 - 알킬 또는 트리플루오로메틸인 일반식(I)의 화합물, 및 일반식(I)의 카복실산의 생리학적으로 허용되는 염
- 제 1 항 또는 제 2 항에 있어서, R¹이 하이드록시 또는 저급- 알콕시인 화합물
- 제 1 항 내지 제 3 항중 어느 한 항에 있어서, R²가 수소인 화합물
- 제 1 항 내지 제 4항중 어느 한 항에 있어서, R3,R4,R5,R6,R7,R8,R9,R10,R11및 R12가 수소 또는 저급 - 알킬인 화합물
- 제 1 항 내지 제 4 항중 어느 한 항에 있어서, 잔기 R³내지 R12중 적어도 하나가 저급 - 알킬인 화합물
- 제 1 항 내지 제 4 항 중 어느 한 항에 있어서 R¹ 및 R12가 하이드록시인 화합물
- 제 1 항 내지 제 4항중 어느 한 항에 있어서 R11이 수소이고, R12가 하이드록시인 화합물
- 제 1 항 내지 제 4 항중 어느 한 항에 있어서, R³ 및 (R5) 가 함께는 메틸렌 그룹인 화합물
- 에틸 P-[(E)-2-(6,7,8,9-테트라하이드로-9,9-디메틸-5H-벤조사이클로헵텐-2-일)프로페닐]벤조에이트
- 에틸 P-[(E)-2-(6,7,8,9- 테트라하이드로 -9,9-디메틸-5H-벤조사이클로헵텐-2-일)프로페닐]벤조에이트 : 에틸 P-[(E)-2-2(6,7,8,9-테트라하이드로 -5,5-디메틸 -5H-벤조사이클로헵텐-2-일)프로페닐] 벤조에이트: 에틸 P-[(E)-2-(6,7,8,9-테트라하이드로-5,9,9-트리메틸-5H-벤조사이크로헵텐-2-일)프로페닐]벤조에이트:P-[(E)-2-(6,7,8,9-테트라하이드로 - 5,5,9-트리메틸-5H-벤조사이클로헵텐-2-일)프로페닐]벤조에이트 : 에틸 P-[(E)-2-2(6,7,8,9-테트라하이드로-5,5,9,9-테트라메틸-5H-벤조사이클로헵텐- 2-일)프로페닐]벤조에이트 : 에틸 P-[(E)-2-(6,7,8,9-테트라하이드로 - 7,7,9-테트라메틸-5H-벤조사이클로헵텐-2-일)프로페닐]벤조에이트 : 메틸 P-[(E)-2-(6,7,8,9-테트라하이드로 - 7,7,9,9-테트라메틸 - 5H-벤조사이클로헵텐-2-일)프로페닐]벤조에이트 : 에틸 P-[(E)-2-(7-에틸-6,7,8,9-테트라하이드로- 7-메틸-5H- 벤조사이클로헵텐-2-일)프로페닐]벤조에이트: P-[(E)-6,7,8,9-테트라하이드로-5H-벤조사이클로헵텐-2-일)프로페닐]벤조산 : P-[(E)-2-(6,7,8,9-테트라하이드로-7,7-디메틸-5H-벤조사이클로헵텐-2-일)프로페닐]벤조산 :P-[(E)-2-(6,7,8,9-테트라하이드로--5,5,9,9-디메틸-5H-벤조사이클로헵텐-2-일)프로페닐]벤조산 : 에틸 P-[(E)-2-(6,7,8,9-테트라하이드로-7-메틸-5H-벤조사이클로헵텐 -2-일)프로페닐]벤조에이트 : P-[(E)-2-(6,7,8,9-테트라하이드로 - 6,6,8,8-테트라메틸 - 5H-벤조사이클로헵텐-2-일)프로페닐]벤조산 : 메틸 P-[(E)-2-(6,7,8,9-테트라하이드로-3,7,7-트리메틸-5H-벤조시이클로헵텐-2-일)프로페닐]벤조에이트 : 에틸 P-[(E)-2-(6,7,8,9-테트라하이드로-9-메틸-5H-벤조사이클로헵텐-2-일)프로페닐]벤조에이트: P-[(E)-2-(6,7,8,9-테트라하이드로-7,7,9,9-테트라메틸-5H-벤조사이클로헵텐-2-일)프로페닐]벤조산 : P-[(ZX)-2-(6,7,8,9-테트라하이드로-7,7-디메틸-3-옥틸-5H-벤조사이클로헵텐-2-일)프로페닐]벤조산 : P-[(Z)-2-(3-브로모-6,7,8,9-테트라하이드로-7,7-디메틸-5H-벤조사이클로헵텐-2-일)프로페닐]벤조산 : P-[(Z)-2-(6,7,8,9-테트라하이드로-3,7,7-트리메틸-5H-벤조사이클로헵텐-2-일)프로페닐]벤조산 : 및 에틸 P-[(E)-2-(6,7,8,9-테트라하이드로-5H-벤조사이클로헵텐-2-일)프로페닐]벤조에이트로 이루어진 그룹중에서 선택되는 화합물
- 에틸 P-[(E)-2-[5,6,8,9-테트라하이드로스피로-[7H-벤조사이클로헵텐-7,1-사이클로프로판]-2-일]프로페닐]벤조에이트로 이루어진 그룹중에서 선택되는 화합물
- 에틸 P-[(E)-2-(6,7,8,9-테트라하이드로-7-옥소-5H-벤조사이클로헵텐-2-일)프로페닐]벤조에이트 : 및 에틸 P-[(E)-2-(6,7,8,9-테트라하이드로-6,6,8,8,-테트라메틸7-5H-벤조사이클로헵텐-2-일)프로페닐]벤조에이트로 이루어진 그룹중에서 선택되는 화합물
- 에틸 P-[(E)-2-(6,7,8,9-테트라하이드로-10-아세톡시-5,9-디메틸-5,9-메타노-5H-벤조사이클로헵텐-2-일)프로페닐]벤조에이트 : P-[(E)-2-(6,7,8,9-테트라하이드로-10-하이드록시-5,9-디메틸-5,9-메타노-5H-벤조시아클로헵텐-2-일)프로페닐]벤조산 : 에틸 P-[(E)-2-(6,7,8,9-테트라하이드로-5,9-디메틸-5,9-메타노-5H-벤조사이클로헵텐-2-일)프로페닐]벤조에이트 및 P-[(E)-2-(6,7,8,9-테트라하이드로-5,9-디메틸-5,0-메티노-5H-벤조사이클로헵텐-2-일)프로페닐]벤조산으로 이루어진 그룹중에서 선택되는 화합물
- 제 1 항 내지 제14항중 어느 한 항에 있어서 약제학적으로 하기 위한 화합물
- 일반식(II)의 화합물과 일반식(III)의 화합물을 반응시키고, 존재할 수 있는 하이드록시 또는 옥소 보호그룹을 축합 생성물로부터 분해 제거하고, 필요한 경우, 이렇게 하여 수득된 일반식(I)의 화합물의 에스테르 그룹-COR′을 비누화(saponifying)시키거나, 또는 카복스 아미노그룹 또는 N-모노 또는 디알킬화 카복스 아미노 그룹으로 전환시키거나, 또는 일반식(I)의 카복실신을 생리학적으로 허용하되는 염으로 전환시킴을 특징으로 하여, 일반식(I)의 화합물 및 일반식(I)의 카복실산의 생리학적으로 허용되는 염을 제조하는 방법.상기식에서, A는 잔기 -CH(R13)P+(Q)3Y- 이고, B는 잔기 -CO(R14)- 이거나, 또는 A는 잔기 -CO(R13)-이고 B는 잔기 -PO(OAlk)₂ 이며 : Q는 아릴이고 Y-유기산 또는 무기산의 음이온이며: Alk는 저급 알킬 그룹이고 : R¹내지 R14는 상기 정의한 바와 같으며, 이중에는 R12또는R11및 R12로서 존재하는 하이드록시 또는 옥소그룹은 보호된 형태로 존재한다
- 제 1 항에서 청구된 화합물 및 통상의 담체 물질을 함유하는 약제학적 조성물
- 제16항의 방법에 의해 또는 이의 명백한 화학적 등가 방법에 의해 제조된 제 1 항 내지 제14항중 어느한 항에서 청구된 화합물
- 지루-치료, 각화-치료, 종량-치료, 항알레르기 및 소염활성을 갖는 약제학적 조성물중에서 활성물질로서 사용하기 위한 제1항 내지 제14항중 어느 한 항에서 청구된 화합물
- 실질적으로 본 명세서에 기술되어 있는 신규한 화합물 조성물 및 제조방법※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH434687 | 1987-11-06 | ||
CH04346/87-0 | 1987-11-06 | ||
CH301888 | 1988-08-10 | ||
CH3018/88 | 1988-08-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR890008072A true KR890008072A (ko) | 1989-07-08 |
Family
ID=25691955
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019880014556A KR890008072A (ko) | 1987-11-06 | 1988-11-05 | 벤조사이클로헵텐 유도체 |
Country Status (21)
Country | Link |
---|---|
US (1) | US4992574A (ko) |
EP (1) | EP0315071B1 (ko) |
JP (1) | JPH0678274B2 (ko) |
KR (1) | KR890008072A (ko) |
AT (1) | ATE108763T1 (ko) |
AU (1) | AU614997B2 (ko) |
CA (1) | CA1298309C (ko) |
CZ (1) | CZ703288A3 (ko) |
DE (1) | DE3850740D1 (ko) |
DK (1) | DK618588A (ko) |
ES (1) | ES2056871T3 (ko) |
FI (1) | FI885021A (ko) |
HU (1) | HU204251B (ko) |
IE (1) | IE63436B1 (ko) |
IL (1) | IL88239A (ko) |
MC (1) | MC1990A1 (ko) |
NO (1) | NO171158C (ko) |
NZ (1) | NZ226769A (ko) |
PH (1) | PH25523A (ko) |
PT (1) | PT88944B (ko) |
YU (1) | YU202888A (ko) |
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DE3602473A1 (de) * | 1986-01-28 | 1987-07-30 | Basf Ag | Vinylphenolderivate, ihre herstellung und verwendung |
ZW7487A1 (en) * | 1986-05-23 | 1987-12-16 | Hoffmann La Roche | Tetrahydronaphthaline and indane derivatives |
-
1988
- 1988-10-06 CA CA000579471A patent/CA1298309C/en not_active Expired - Lifetime
- 1988-10-14 AU AU23721/88A patent/AU614997B2/en not_active Ceased
- 1988-10-24 CZ CS887032A patent/CZ703288A3/cs unknown
- 1988-10-27 US US07/263,651 patent/US4992574A/en not_active Expired - Fee Related
- 1988-10-28 ES ES88118011T patent/ES2056871T3/es not_active Expired - Lifetime
- 1988-10-28 DE DE3850740T patent/DE3850740D1/de not_active Expired - Fee Related
- 1988-10-28 NZ NZ226769A patent/NZ226769A/en unknown
- 1988-10-28 EP EP88118011A patent/EP0315071B1/de not_active Expired - Lifetime
- 1988-10-28 AT AT88118011T patent/ATE108763T1/de not_active IP Right Cessation
- 1988-10-31 IL IL88239A patent/IL88239A/xx unknown
- 1988-11-01 FI FI885021A patent/FI885021A/fi not_active Application Discontinuation
- 1988-11-01 YU YU02028/88A patent/YU202888A/xx unknown
- 1988-11-02 MC MC882014A patent/MC1990A1/xx unknown
- 1988-11-02 HU HU885670A patent/HU204251B/hu not_active IP Right Cessation
- 1988-11-04 NO NO884936A patent/NO171158C/no unknown
- 1988-11-04 PT PT88944A patent/PT88944B/pt not_active IP Right Cessation
- 1988-11-04 PH PH37776A patent/PH25523A/en unknown
- 1988-11-04 DK DK618588A patent/DK618588A/da not_active Application Discontinuation
- 1988-11-04 JP JP63279181A patent/JPH0678274B2/ja not_active Expired - Lifetime
- 1988-11-04 IE IE333988A patent/IE63436B1/en not_active IP Right Cessation
- 1988-11-05 KR KR1019880014556A patent/KR890008072A/ko not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
HU204251B (en) | 1991-12-30 |
YU202888A (en) | 1990-04-30 |
IL88239A0 (en) | 1989-06-30 |
EP0315071A2 (de) | 1989-05-10 |
EP0315071A3 (de) | 1991-02-27 |
DK618588D0 (da) | 1988-11-04 |
NO884936D0 (no) | 1988-11-04 |
PT88944A (pt) | 1988-12-01 |
CA1298309C (en) | 1992-03-31 |
CZ703288A3 (en) | 1993-08-11 |
HUT48196A (en) | 1989-05-29 |
US4992574A (en) | 1991-02-12 |
AU614997B2 (en) | 1991-09-19 |
JPH01157934A (ja) | 1989-06-21 |
DE3850740D1 (de) | 1994-08-25 |
NZ226769A (en) | 1992-02-25 |
IL88239A (en) | 1993-03-15 |
NO171158B (no) | 1992-10-26 |
AU2372188A (en) | 1989-05-11 |
NO884936L (no) | 1989-05-08 |
IE63436B1 (en) | 1995-04-19 |
FI885021A (fi) | 1989-05-07 |
PH25523A (en) | 1991-07-24 |
DK618588A (da) | 1989-05-07 |
ES2056871T3 (es) | 1994-10-16 |
ATE108763T1 (de) | 1994-08-15 |
IE883339L (en) | 1989-05-06 |
MC1990A1 (fr) | 1989-11-30 |
NO171158C (no) | 1993-02-03 |
PT88944B (pt) | 1993-01-29 |
JPH0678274B2 (ja) | 1994-10-05 |
EP0315071B1 (de) | 1994-07-20 |
FI885021A0 (fi) | 1988-11-01 |
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