SK279066B6 - Substituované deriváty kyseliny mandľovej, spôsob - Google Patents
Substituované deriváty kyseliny mandľovej, spôsob Download PDFInfo
- Publication number
- SK279066B6 SK279066B6 SK2639-92A SK263992A SK279066B6 SK 279066 B6 SK279066 B6 SK 279066B6 SK 263992 A SK263992 A SK 263992A SK 279066 B6 SK279066 B6 SK 279066B6
- Authority
- SK
- Slovakia
- Prior art keywords
- acid derivatives
- formula
- mandelic acid
- atom
- substituted mandelic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 239000002253 acid Substances 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical class O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 10
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 5
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- -1 quinolin-2-ylmethoxy Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000003776 cleavage reaction Methods 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 230000007017 scission Effects 0.000 claims description 6
- 239000007818 Grignard reagent Substances 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 238000007796 conventional method Methods 0.000 claims description 5
- 150000004795 grignard reagents Chemical class 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 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 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052793 cadmium Inorganic materials 0.000 claims description 4
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
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- 230000002401 inhibitory effect Effects 0.000 claims description 2
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- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
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- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 229940079593 drug Drugs 0.000 abstract 2
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical class C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 abstract 1
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 3
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 3
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- 230000004060 metabolic process Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- FONOLISTZOYVEM-UHFFFAOYSA-N methyl 2-oxo-2-[4-(quinolin-2-ylmethoxy)phenyl]acetate Chemical compound C1=CC(C(=O)C(=O)OC)=CC=C1OCC1=CC=C(C=CC=C2)C2=N1 FONOLISTZOYVEM-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (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)
- Quinoline Compounds (AREA)
- Measurement Of Force In General (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Manufacture And Refinement Of Metals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4128681A DE4128681A1 (de) | 1991-08-29 | 1991-08-29 | Substituierte mandelsaeurederivate, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK279066B6 true SK279066B6 (sk) | 1998-06-03 |
| SK263992A3 SK263992A3 (en) | 1998-06-03 |
Family
ID=6439400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK2639-92A SK263992A3 (en) | 1991-08-29 | 1992-08-26 | Substituted derivatives of mandelic acid, a method of producing the same, their use in drugs and pharmaceutical compositions containing same |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5292769A (cs) |
| EP (1) | EP0529450B1 (cs) |
| JP (1) | JPH05194402A (cs) |
| KR (1) | KR930004270A (cs) |
| AT (1) | ATE115949T1 (cs) |
| AU (1) | AU643628B2 (cs) |
| CA (1) | CA2076929A1 (cs) |
| CZ (1) | CZ281501B6 (cs) |
| DE (2) | DE4128681A1 (cs) |
| DK (1) | DK0529450T3 (cs) |
| ES (1) | ES2065737T3 (cs) |
| FI (1) | FI101222B (cs) |
| GR (1) | GR3015457T3 (cs) |
| HU (1) | HU214577B (cs) |
| IL (1) | IL102949A (cs) |
| MX (1) | MX9204748A (cs) |
| MY (1) | MY110206A (cs) |
| RU (1) | RU2066315C1 (cs) |
| SK (1) | SK263992A3 (cs) |
| TW (1) | TW207995B (cs) |
| ZA (1) | ZA926536B (cs) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4219765A1 (de) * | 1992-06-17 | 1993-12-23 | Bayer Ag | Substituierte (Benzothiazolyl- und Chinoxalyl-methoxy)phenylessigsäurederivate |
| US5512581A (en) * | 1994-07-18 | 1996-04-30 | Abbott Laboratories | Iminoxycarboxylates and derivatives as inhibitors of leukotriene biosynthesis |
| DE4443891A1 (de) * | 1994-12-09 | 1996-06-13 | Bayer Ag | Heterocyclisch substituierte Oxy-phenyl-(phenyl)glycinolamide |
| DE4443892A1 (de) * | 1994-12-09 | 1996-06-13 | Bayer Ag | 4-(Chinolin-2-yl-methoxy)-phenyl-essigsäurederivate |
| HRP970330B1 (en) * | 1996-07-08 | 2004-06-30 | Bayer Ag | Cycloalkano pyridines |
| US8719041B2 (en) * | 2002-06-10 | 2014-05-06 | Ebay Inc. | Method and system for customizing a network-based transaction facility seller application |
| TW200410921A (en) * | 2002-11-25 | 2004-07-01 | Hoffmann La Roche | Mandelic acid derivatives |
| CA2547518A1 (en) | 2003-12-12 | 2005-06-30 | Wyeth | Quinolines useful in treating cardiovascular disease |
| WO2006063828A1 (de) * | 2004-12-18 | 2006-06-22 | Bayer Healthcare Ag | 4-cycloalkyl-substituierte tetrahydrochinolinderivate und deren verwendung als medikamente |
| WO2008067566A1 (en) | 2006-11-30 | 2008-06-05 | Amira Pharmaceuticals, Inc. | Compositions and treatments comprising 5-lipoxygenase-activating protein inhibitors and nitric oxide modulators |
| CN106456624B (zh) | 2014-02-04 | 2020-05-22 | 生物制药合伙公司 | Flap抑制剂的降低中枢神经系统内的神经炎症介导的损伤的应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3318145A1 (de) * | 1983-05-18 | 1984-11-22 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-6,8-difluor-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3927931A1 (de) * | 1989-08-24 | 1991-02-28 | Bayer Ag | Disubstituierte (chinolin-2-yl-methoxy)phenylessigsaeure-derivate |
-
1991
- 1991-08-29 DE DE4128681A patent/DE4128681A1/de not_active Withdrawn
-
1992
- 1992-07-28 TW TW081105930A patent/TW207995B/zh active
- 1992-08-11 MY MYPI92001437A patent/MY110206A/en unknown
- 1992-08-17 MX MX9204748A patent/MX9204748A/es not_active IP Right Cessation
- 1992-08-17 ES ES92113956T patent/ES2065737T3/es not_active Expired - Lifetime
- 1992-08-17 DE DE59201013T patent/DE59201013D1/de not_active Expired - Fee Related
- 1992-08-17 AT AT92113956T patent/ATE115949T1/de not_active IP Right Cessation
- 1992-08-17 EP EP92113956A patent/EP0529450B1/de not_active Expired - Lifetime
- 1992-08-17 DK DK92113956.4T patent/DK0529450T3/da active
- 1992-08-21 US US07/934,059 patent/US5292769A/en not_active Expired - Fee Related
- 1992-08-24 JP JP4247241A patent/JPH05194402A/ja active Pending
- 1992-08-26 CA CA002076929A patent/CA2076929A1/en not_active Abandoned
- 1992-08-26 SK SK2639-92A patent/SK263992A3/sk unknown
- 1992-08-26 IL IL10294992A patent/IL102949A/xx not_active IP Right Cessation
- 1992-08-26 CZ CS922639A patent/CZ281501B6/cs unknown
- 1992-08-27 FI FI923841A patent/FI101222B/fi active
- 1992-08-27 AU AU21371/92A patent/AU643628B2/en not_active Ceased
- 1992-08-28 ZA ZA926536A patent/ZA926536B/xx unknown
- 1992-08-28 HU HU9202780A patent/HU214577B/hu not_active IP Right Cessation
- 1992-08-28 KR KR1019920015533A patent/KR930004270A/ko not_active Ceased
- 1992-08-28 RU SU925052469A patent/RU2066315C1/ru active
-
1995
- 1995-03-20 GR GR940404001T patent/GR3015457T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW207995B (cs) | 1993-06-21 |
| CA2076929A1 (en) | 1993-03-01 |
| IL102949A0 (en) | 1993-01-31 |
| AU2137192A (en) | 1993-03-04 |
| FI101222B1 (fi) | 1998-05-15 |
| GR3015457T3 (en) | 1995-06-30 |
| KR930004270A (ko) | 1993-03-22 |
| US5292769A (en) | 1994-03-08 |
| DK0529450T3 (da) | 1995-05-15 |
| EP0529450B1 (de) | 1994-12-21 |
| FI923841A7 (fi) | 1993-03-01 |
| MY110206A (en) | 1998-02-28 |
| JPH05194402A (ja) | 1993-08-03 |
| IL102949A (en) | 1997-02-18 |
| ATE115949T1 (de) | 1995-01-15 |
| CZ281501B6 (cs) | 1996-10-16 |
| HU9202780D0 (en) | 1992-12-28 |
| FI923841A0 (fi) | 1992-08-27 |
| HU214577B (hu) | 1998-04-28 |
| FI101222B (fi) | 1998-05-15 |
| HUT67137A (en) | 1995-02-28 |
| MX9204748A (es) | 1993-02-01 |
| DE4128681A1 (de) | 1993-03-04 |
| SK263992A3 (en) | 1998-06-03 |
| CZ263992A3 (en) | 1993-08-11 |
| EP0529450A1 (de) | 1993-03-03 |
| AU643628B2 (en) | 1993-11-18 |
| ES2065737T3 (es) | 1995-02-16 |
| ZA926536B (en) | 1993-03-05 |
| DE59201013D1 (de) | 1995-02-02 |
| RU2066315C1 (ru) | 1996-09-10 |
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