SU582762A3 - Способ получени производных бензоксазола - Google Patents
Способ получени производных бензоксазолаInfo
- Publication number
- SU582762A3 SU582762A3 SU7402079273A SU2079273A SU582762A3 SU 582762 A3 SU582762 A3 SU 582762A3 SU 7402079273 A SU7402079273 A SU 7402079273A SU 2079273 A SU2079273 A SU 2079273A SU 582762 A3 SU582762 A3 SU 582762A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- solution
- benzoxazolyl
- preparing
- propionic acid
- Prior art date
Links
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title abstract description 3
- 238000000034 method Methods 0.000 title description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 8
- -1 6-benzoxazolyl Chemical group 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000001760 anti-analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ZBRNHUSCZGYNLG-UHFFFAOYSA-N 2-(3-amino-4-hydroxyphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(O)C(N)=C1 ZBRNHUSCZGYNLG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- NGFBZTMAKWKGLF-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)propanoic acid Chemical compound C1=CC=C2OC(C(C(O)=O)C)=NC2=C1 NGFBZTMAKWKGLF-UHFFFAOYSA-N 0.000 description 1
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
- HETBKLHJEWXWBM-UHFFFAOYSA-N 4-chloro-3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC(C=O)=CC=C1Cl HETBKLHJEWXWBM-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- DMJBUAAUSMMJFJ-UHFFFAOYSA-N ethyl 2-(4-amino-3-hydroxyphenyl)propanoate Chemical compound CCOC(=O)C(C)C1=CC=C(N)C(O)=C1 DMJBUAAUSMMJFJ-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ БЕНЗОКСАЗОЛА
комплексным-гидридом металла Б соответствующий спирт или превращают в соль, обрабатыва со-ответствующим основанием, таким как гидроокись металла или щелочноземельного металла, или легко превращают в свободную кислоту, обрабатыва другой кислотой , такой как сол на или серна кислота. Кислоту общей формулы (1) или ее соль можно превратить в эфир, обрабатыва соответствующим спиртом или галогенидом; кислоту можно также превратить в амид реакцией с аммиаком или соответствующим первичным или вторичным амином.
Соединение общей формулы (.1) , гд й и/или Ц, водород, может алкилироватьс дл получени соответствующего соединени общей формулы (I), гл RJ и/или Да - Cj-Сд -алкил. Алкилирование осуществл ют путем взаимодействи щелочнометаллического производного соответствующего производног беиэоксазола с алкилгалогенидом, например метил- или этилйодидом.
и м е р 1. 2-(2-о-хлорфенил-б-бёнзоксазолил ) -пропионова кйслота
А. Этил-2-(2-о-хлорфенил-б-бенэоксазолил )-пропионат.
Раствор о-хлорбензальдегида (4,3г и этил-2-(3-окси-4-аминофенил)-пропионата (6 г) в толуоле {100 мл) кип т т с насадкой Дина-Старка, собира образующуюс воду. Через 30 мин раствор упаривают досуха. Остаток раствор ют в уксусной кислоте (100мл добавл ют тетраацетат свинца (15 г) и нагревают на вод ной бане 1 ч. Затем раствор выливают в смесьльда с водой и экстрагируют эфиром, получа продукт в виде масла, образец которого дает удовлетворительный микроанёшиз .
Б. 2-(2-о-хлорфенил-б-беизоксазолил )-пропионова кислота.
Получеиный этил-2-(2-о-хлорфенил-б-бензоксаэолил )-пропионат перемешивают с раствором гидроокири натри (50 мл), через 1,5 ч раствор упаривают досуха и подкислением и перекристаллизацией из эфира получают целевой продукт с т.пл. 108-110 0.
Найдено, % С 63,5; Н 4,1; N. 4,8; се 12,0
Вычислено,%1 С 63,7; Н 4,0; М 4,6; С1 11,8
П р и м ер 2. 2- 2-{3-пирндил)-5-бензоксазолил -пропионойа кислота .
Натрий ( г) раствор ют осторожно в метан.оле (45 мл) и добавлшот 3-цианпирйдин (5,2 г). На следующий деиь добавл ют уксусную кислоту (0,3 г) с последующим добавлеиием 2-(3-амино-4-оксифенил)-пропионовой кислоты (9,05 г). Смесь при перемеХ1швании кип т т с обратным холодилЬ
НИКОМ 5 ч, раствор твердое вещество . К гор чему раствору добавл ют равный объем воды. При охлаждении отдел ют кремовые кристаллы, которые отфильтровывают и перекристаллизацией из смеси диметилформамида и этанола получают целевую кислоту, т.пл. 197-200с.
10Найдено, %: с 67,3; Н 4,3;
N 10,3
Вычислено,%: с 67,2; Н 4.5;
К 10,4
Аналогично получают следующие сое«5 динени :
2- 2-(4-лиридил)-5 бензоксазолил -пропионова кислота, т.гш. 247-250с Найдено, %:С66,9;Н4,8г
N 10,2 0Вычислено,%; с 67,2; Н 4,5;
N 10,4
(2-пиридил)-5-бензоксазолил -пропионова кислота, т.пл.177-179°С.
Найдено, %: С 67,0; Н 4,5; 5N10,2
Вычислено,%: С 67,2; Н 4,5;
N 10,4
2-(2- П -хлорфенил-5-; бензоксазолил )-пропионова кислота, т.плЛввс 0 Найдено, %: с 63,50; Н 4,16;
N 4,72
Вычислено,%: С 63,68; Н 4,00; N 4,64
5Примерз. (3-нитро-4-хлорфенил )-бензоксазол-5-ил -пропионова кислота.
Раствор З-нитро-4-хлорбензальдегида (0,925 г) и 2-(З-амино-4-оксифенил )-пропионовой кислоты (0,900г) в этаноле (25 г) кип т т с обратным холодильником 3,5 ч, упаривают и получают твердое Шиффово основание, которое раствор ют в гор чей уксусной кислоте (50 мл). Добавл ют тетраацетат свинца (2,8 г) и охлаждают до комнатной температуры. На следующее утро добавл ют воду (200 мл) и выдел ют липкое твердое вещество, которое сушат и растирают с небольшим количеством хлороформа, получа чистую беизоксазольную кислоту (0,5 г), т.пл. 210-213С, Найдено, % с 55,2; Н 3,2;
N 8,05 Вычислено,%; С 55,4; Н 3,2;
Ы 8,1
Аналогично получают 2- (2-нитрофенил -5-бензоксазолил)-пррпионовую кислоту, т.пл. 211-217 С.
Найдено, %; С 61,29; Н 3,75;
М 8,68
Вычислено,%8 С 61,53; Н 3,87; N 8,97
Claims (1)
1. Гетероциклические соединени . Под ред. Р.Эльдерфильда, М., Иностранна литература , 1961, с.349.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2340972A GB1435721A (en) | 1972-05-18 | 1972-05-18 | Benzoxazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU582762A3 true SU582762A3 (ru) | 1977-11-30 |
Family
ID=10195157
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7301916802A SU574157A3 (ru) | 1972-05-18 | 1973-05-17 | Способ получени производных бензоксазола |
| SU7402079274A SU580837A3 (ru) | 1972-05-18 | 1974-11-29 | Способ получени 5-или 6-бензоксазоловой кислоты или ее солей |
| SU7402079273A SU582762A3 (ru) | 1972-05-18 | 1974-11-29 | Способ получени производных бензоксазола |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7301916802A SU574157A3 (ru) | 1972-05-18 | 1973-05-17 | Способ получени производных бензоксазола |
| SU7402079274A SU580837A3 (ru) | 1972-05-18 | 1974-11-29 | Способ получени 5-или 6-бензоксазоловой кислоты или ее солей |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US3912748A (ru) |
| JP (6) | JPS5912672B2 (ru) |
| KR (1) | KR780000234B1 (ru) |
| AR (4) | AR230991A1 (ru) |
| AT (1) | AT333752B (ru) |
| BE (1) | BE799790A (ru) |
| BG (1) | BG21408A3 (ru) |
| CA (1) | CA1029019A (ru) |
| CH (5) | CH592071A5 (ru) |
| CS (1) | CS200455B2 (ru) |
| CY (1) | CY1016A (ru) |
| DD (1) | DD105229A5 (ru) |
| DE (1) | DE2324443A1 (ru) |
| DK (1) | DK140340B (ru) |
| ES (1) | ES414863A1 (ru) |
| FR (2) | FR2184966B1 (ru) |
| GB (1) | GB1435721A (ru) |
| HK (1) | HK72579A (ru) |
| HU (1) | HU167933B (ru) |
| IE (2) | IE37564B1 (ru) |
| IL (2) | IL42102A (ru) |
| KE (1) | KE2975A (ru) |
| MY (1) | MY8000063A (ru) |
| NL (1) | NL170145C (ru) |
| PH (3) | PH9685A (ru) |
| PL (3) | PL89247B1 (ru) |
| RO (2) | RO66278A (ru) |
| SE (3) | SE386174B (ru) |
| SU (3) | SU574157A3 (ru) |
| YU (3) | YU130473A (ru) |
| ZA (1) | ZA732791B (ru) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3888864A (en) | 1973-06-29 | 1975-06-10 | Hoffmann La Roche | Amino lower alkyl ether derivatives of opium alkaloids |
| GB1495488A (en) * | 1976-06-23 | 1977-12-21 | Ippco Int Pharma Patents Co Es | Optically active 2-(2-phenyl-5-benzoxazolyl)propionic acids |
| US4087437A (en) * | 1976-09-07 | 1978-05-02 | Eli Lilly And Company | 2-Phenyl-5-benzoxazolylalkanoic acid purification process |
| GB1590587A (en) * | 1977-06-28 | 1981-06-03 | Lilly Industries Ltd | Benoxaprofen |
| IT1099589B (it) * | 1978-08-04 | 1985-09-18 | Ravizza Spa | Processo per la preparazione di derivati dell'acido benzoxazolil propionico |
| CA1125768A (en) * | 1978-10-31 | 1982-06-15 | Hoffmann-La Roche Limited | Benzoxazole derivatives |
| GB2058381B (en) | 1979-07-18 | 1983-01-19 | Fuji Photo Film Co Ltd | Colour photographic light-sensitive material containing dye-releasing redox compound |
| GR75153B (ru) * | 1981-03-27 | 1984-07-13 | Lilly Co Eli | |
| IT1157295B (it) * | 1982-07-19 | 1987-02-11 | Ravizza Spa | Processo perfezionato per la preparazione di derivati dell'acido benzoxazolil propionico |
| DE3413875A1 (de) * | 1984-04-12 | 1985-10-17 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | Benzothiazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltendes arzneimittel |
| IT1177017B (it) * | 1984-10-22 | 1987-08-26 | Ravizza Spa | Processo per la preparazione dell'acido 2(4-flurofenil)alfa-metil-5-benzox azoloacetico |
| US4873259A (en) * | 1987-06-10 | 1989-10-10 | Abbott Laboratories | Indole, benzofuran, benzothiophene containing lipoxygenase inhibiting compounds |
| US4822809A (en) * | 1987-11-13 | 1989-04-18 | Abbott Laboratories | Benzazole lipoxygenase inhibiting compounds |
| IT1233836B (it) * | 1988-01-13 | 1992-04-21 | Euroresearch Srl | Sali idrosolubili dell'acido (+)2-(4 fluorofenil)-alfa-metil-5 benzoxazolo acetato. |
| UA83620C2 (ru) * | 2001-12-05 | 2008-08-11 | Уайт | Замещенные бензоксазолы и их аналоги как эстрогенные агенты |
| WO2004046122A2 (en) * | 2002-11-16 | 2004-06-03 | Oxford Glycosciences (Uk) Ltd | Benzoxazole, benzthiazole and benzimidazole acid derivatives and their use as heparanase inhibitors |
| WO2004076386A2 (en) | 2003-02-25 | 2004-09-10 | Topotarget Uk Limited | Carbamic acid compounds comprising a bicyclic heteroaryl group as hdac inhibitors |
| DK1856031T3 (da) * | 2004-12-15 | 2009-06-29 | Dompe Pha R Ma Spa Res & Mfg | 2-arylpropionsyrederivater og farmaceutiske sammensætninger indeholdende disse |
| EP1888548B1 (en) | 2005-05-26 | 2012-08-22 | Neuron Systems, Inc | Quinoline derivative for the treatment of retinal diseases |
| JP5369854B2 (ja) | 2008-04-21 | 2013-12-18 | 住友化学株式会社 | 有害節足動物防除組成物および縮合複素環化合物 |
| EP2948149A4 (en) | 2013-01-23 | 2016-12-14 | Aldeyra Therapeutics Inc | BY TOXIC ALDEHYDIC DISEASES AND TREATMENT |
| CN105228989A (zh) | 2013-01-25 | 2016-01-06 | 奥尔德拉医疗公司 | 黄斑变性治疗中的新颖捕获剂 |
| CN107001267A (zh) * | 2014-08-08 | 2017-08-01 | 马合伙人株式会社 | 稠合杂环化合物 |
| KR102664994B1 (ko) | 2015-08-21 | 2024-05-13 | 알데이라 테라퓨틱스, 아이엔씨. | 중수소화 화합물 및 이의 용도 |
| CN109152774A (zh) | 2016-05-09 | 2019-01-04 | 奥尔德拉医疗公司 | 眼部炎性病症和疾病的组合治疗 |
| JP2020511461A (ja) | 2017-03-16 | 2020-04-16 | アルデイラ セラピューティクス， インコーポレイテッド | 多形化合物およびその使用 |
| MX2020003425A (es) | 2017-10-10 | 2020-07-29 | Aldeyra Therapeutics Inc | Tratamiento de trastornos inflamatorios. |
| US12006298B2 (en) | 2018-08-06 | 2024-06-11 | Aldeyra Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| CN115869258A (zh) | 2018-09-25 | 2023-03-31 | 奥尔德拉医疗公司 | 用于治疗干眼病的调配物 |
| JP2022526917A (ja) | 2019-03-26 | 2022-05-27 | アルデイラ セラピューティクス， インコーポレイテッド | 眼科用製剤およびその使用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD70860A (ru) * | ||||
| NL285932A (ru) * | 1961-11-27 | |||
| CH516339A (de) * | 1969-03-03 | 1971-12-15 | Ciba Geigy Ag | Verwendung von Azolverbindungen als Antioxydantien |
| DE2118315C3 (de) * | 1970-04-20 | 1975-04-03 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | 2-(1H)-Chinazolinonderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| IL37633A (en) * | 1970-09-10 | 1975-08-31 | Merck & Co Inc | 2-(4-(2-benzoxazolyl)phenyl)alkanoic acid derivatives |
| DE2115926C3 (de) * | 1971-04-01 | 1978-05-03 | C.H. Boehringer Sohn, 6507 Ingelheim | 1 -(4-Hydroxy-3-dimethylaminosuIfamidophenyI)-2-aminoäthanderivate, Verfahren zu ihrer Herstellung und diese enthaltende Mittel |
| GB1491863A (en) * | 1973-10-23 | 1977-11-16 | Lilly Industries Ltd | 2,5-or 2,6-disubstituted benzoxazoles |
| GB1590587A (en) * | 1977-06-28 | 1981-06-03 | Lilly Industries Ltd | Benoxaprofen |
-
1972
- 1972-05-18 GB GB2340972A patent/GB1435721A/en not_active Expired
-
1973
- 1973-04-25 IE IE1898/76A patent/IE37564B1/xx unknown
- 1973-04-25 ZA ZA732791A patent/ZA732791B/xx unknown
- 1973-04-25 IL IL42102A patent/IL42102A/en unknown
- 1973-04-28 IE IE648/73A patent/IE37563B1/xx unknown
- 1973-05-01 US US356251A patent/US3912748A/en not_active Expired - Lifetime
- 1973-05-01 CA CA170,186A patent/CA1029019A/en not_active Expired
- 1973-05-07 PH PH14592*UA patent/PH9685A/en unknown
- 1973-05-11 AR AR247979A patent/AR230991A1/es active
- 1973-05-15 CY CY1016A patent/CY1016A/xx unknown
- 1973-05-15 DE DE2324443A patent/DE2324443A1/de not_active Ceased
- 1973-05-16 KR KR7300790A patent/KR780000234B1/ko active
- 1973-05-16 HU HULI244A patent/HU167933B/hu not_active IP Right Cessation
- 1973-05-16 CS CS733508A patent/CS200455B2/cs unknown
- 1973-05-16 DD DD170872A patent/DD105229A5/xx unknown
- 1973-05-17 YU YU01304/73A patent/YU130473A/xx unknown
- 1973-05-17 CH CH703673A patent/CH592071A5/xx not_active IP Right Cessation
- 1973-05-17 AT AT432573A patent/AT333752B/de not_active IP Right Cessation
- 1973-05-17 CH CH1621375A patent/CH587834A5/xx not_active IP Right Cessation
- 1973-05-17 JP JP48055110A patent/JPS5912672B2/ja not_active Expired
- 1973-05-17 DK DK274673AA patent/DK140340B/da not_active IP Right Cessation
- 1973-05-17 ES ES414863A patent/ES414863A1/es not_active Expired
- 1973-05-17 CH CH1298576A patent/CH595362A5/xx not_active IP Right Cessation
- 1973-05-17 CH CH1621275A patent/CH595361A5/xx not_active IP Right Cessation
- 1973-05-17 CH CH1298676A patent/CH594643A5/xx not_active IP Right Cessation
- 1973-05-17 SE SE7307005A patent/SE386174B/xx unknown
- 1973-05-17 FR FR7317894A patent/FR2184966B1/fr not_active Expired
- 1973-05-17 SU SU7301916802A patent/SU574157A3/ru active
- 1973-05-18 PL PL1973162653A patent/PL89247B1/pl unknown
- 1973-05-18 BG BG23657A patent/BG21408A3/xx unknown
- 1973-05-18 PL PL1973182614A patent/PL92565B1/pl unknown
- 1973-05-18 PL PL1973183011A patent/PL94208B1/pl unknown
- 1973-05-18 NL NLAANVRAGE7307018,A patent/NL170145C/xx not_active IP Right Cessation
- 1973-05-18 RO RO7374829A patent/RO66278A/ro unknown
- 1973-05-18 BE BE6044169A patent/BE799790A/xx not_active IP Right Cessation
- 1973-05-18 RO RO7384621A patent/RO66800A/ro unknown
-
1974
- 1974-11-21 PH PH16541A patent/PH11718A/en unknown
- 1974-11-21 PH PH16542A patent/PH10704A/en unknown
- 1974-11-29 SU SU7402079274A patent/SU580837A3/ru active
- 1974-11-29 SU SU7402079273A patent/SU582762A3/ru active
-
1975
- 1975-01-01 AR AR257862A patent/AR207857A1/es active
- 1975-01-01 AR AR257863A patent/AR205021A1/es active
- 1975-06-12 FR FR7518361A patent/FR2284592A1/fr active Granted
- 1975-08-22 SE SE7509387A patent/SE434399B/xx not_active IP Right Cessation
- 1975-12-23 IL IL48711A patent/IL48711A0/xx unknown
-
1976
- 1976-03-06 AR AR257861A patent/AR212010A1/es active
-
1977
- 1977-09-21 SE SE7710602A patent/SE435838B/xx not_active IP Right Cessation
-
1979
- 1979-05-17 YU YU01170/79A patent/YU117079A/xx unknown
- 1979-05-17 YU YU1171/79A patent/YU36298B/xx unknown
- 1979-07-03 KE KE2975A patent/KE2975A/xx unknown
- 1979-10-11 HK HK725/79A patent/HK72579A/xx unknown
-
1980
- 1980-12-31 MY MY198063A patent/MY8000063A/xx unknown
-
1981
- 1981-05-13 JP JP56072123A patent/JPS5929185B2/ja not_active Expired
- 1981-05-13 JP JP7212481A patent/JPS56167675A/ja active Pending
- 1981-05-13 JP JP7212281A patent/JPS56167674A/ja active Pending
- 1981-05-13 JP JP7212181A patent/JPS56167673A/ja active Pending
-
1984
- 1984-02-02 JP JP59017637A patent/JPS6021976B2/ja not_active Expired
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