PL94510B1 - Sposob wytwarzania nowych amidow kwasu 3-(4-bifenylilo)-2-propenokarboksylowego - Google Patents
Sposob wytwarzania nowych amidow kwasu 3-(4-bifenylilo)-2-propenokarboksylowego Download PDFInfo
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- PL94510B1 PL94510B1 PL1973186474A PL18647473A PL94510B1 PL 94510 B1 PL94510 B1 PL 94510B1 PL 1973186474 A PL1973186474 A PL 1973186474A PL 18647473 A PL18647473 A PL 18647473A PL 94510 B1 PL94510 B1 PL 94510B1
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- biphenylyl
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- acid amides
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- propenocarboxylic
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- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
- C07C245/14—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton
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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
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- A61P3/00—Drugs for disorders of the metabolism
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- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
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- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
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- C07C255/00—Carboxylic acid nitriles
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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
- C07C45/45—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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- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/76—Acyl halides containing halogen outside the carbonyl halide groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
Description
Przedmiotem wynalazku jest sposób wytwarzania nowycb amidów kwasu 3-(4-bifenylilo)-2-propenokarbo- ksylowego o wartosciowych wlasciwosciach farmakologicznych, zwlaszcza o dzialaniu przeciwzapaleniowym.Zwiazki te stanowia poza tym produkty posrednie do wytwarzania dzialajacych przeciwzapalnie kwasów 3-(4-bifenylilo)-maslowych i ich pochodnych.Nowym zwiazkom odpowiada wzór ogólny 1, w którym Ri oznacza atom fluoru lub chloru.Wedlug wynalazku nowe zwiazki o wzorze ogólnym 1 wytwarza sie przez reakcje estru lub halogenku kwasu 3-(4-bifenylilo)-2-propenokarboksylowego o wzorze ogólnym 2, w którym R! ma wyzej podane znaczenie, a X oznacza grupe alkoksylowa lub atom chlorowca z amoniakiem. Reakcje prowadzi sie skutecznie w obojetnym rozpuszczalniku, zwlaszcza w alkoholu, w podwyzszonej temperaturze i podwyzszonym cisnieniu.Nowe zwiazki o wzorze ogólnym 1 wykazuja szczególnie wartosciowe wlasciwosci farmakologiczne, zwlaszcza bardzo dobre dzialanie przeciwzapalne.Nastepujaca np. substancje poddano badaniom na jej bezwzgledne dzialanie przeciwzapalne i jej toksycznosc: amid kwasu 3-(2'-fluoro-4-bifenylilo)-2-propenokarboksylowego = A i jako substancje porównawczo zastosowano fenylobutazon. Zdolnosc tlumienia stanów zapalnych wywolanych w tylnej lapie szczura za pomoca kaolinu lub za pomoca lichen carragen (mech islandzki) oraz ich ostra toksycznosc badano na szczurach po podaniu doustnie badanej substancji a) Obrzek na tylnej lapie szczura wywolany kaolinem. Obrzek wywolano metoda Hillebrechta (Arzneimittel-Forsch. 4, 607 /1954/) przcv wstrzykiwanie pod podeszwe lapy szczura 0,06 ml 10% zawiesiny kaolinu w 0,85% roztworze chlorku sodu. Pomiary grubosci lapy prowadzono metoda Doepfnera i Cerlettiego (Int. Arch., Allergy Immunol. 12, 89 /1958/).2 94 610 Samcom szczurów FW49 o wadze 120-450 9 podawano badane substancje za pomoca zglebnika przelykowo-zoladkowego na 30 minut przed spodowaniem obrzeku. Po uplywie 6 godzin od wywolania obrzeku mierzono wielkosc opuchlizny, porównujac ja z odpowiednia wielkoscia u zwierzat, którym nie podano badanej substancji. Na drodze graficznej ekstrapolacji otrzymanych z róznych dawek procentowych wartosci hamowanie opuchlizny, ustalono dawke prowadzaca do 35% zmniejszenia opuchlizny (ED3 s). b) Obrzek karragenowy. Obrzek wywolywano metoda Wintera i inn. (Proc. Soc. exp. Bipl. Med. 111, 544 /1962/) przez wstrzykiwanie pod podeszwe lapy szczura 0,05 ml 1% roztworu mchu islandzkiego w 0,85% roztworze NaCI. Badane substancje podawano szczurom na 60 minut przed wywolaniem obrzeku. Po uplywie 3 godzin od wywolania obrzeku przeprowadzono pomiary jak w próbce kaolinowej. c) Ostra toksycznosc. Ostra toksycznosc LD50 oznaczono podajac jednakowej liczbie samców i samic szczura FW49 o przecietnej wadze 135g badane substancje zmieszane z tyloza. Wartosc LD50 oznaczono w miare mozliwosci metoda Lichtfield'a i Wilcoxon'a na podstawie liczby zwierzat, które po róznych dawkach padly wciagu 14 dni. d) Wskaznik terapeutyczny stanowiacy miare zakresu terapeutycznego oznaczano jako stosunek wartosci LD50 przy podawaniu doustnym szczurom badanej substancji do sredniej wartosci LD35 ustalonej w badaniu zdolnosci przeciwdzialania stanom zapalnym wywolanym u szczura metoda kaolinowa i karragenowa.Uzyskane w tych badaniach wyniki zebrane sa w podanej nizej tablicy.Poddawany badaniom zwiazek przewyzsza znany fenylobutazon w pozadanym dzialaniu przeciwzapalnym.Poniewaz toksycznosc nie wzrasta równolegle ze wzrostem dzialania przeciwzapalnego, badany zwiazek przewyzsza swym wskaznikiem terapeutycznym znany fenylobutazon, bardzo wydatnie.Substancja Fenylobutazon A Obrzek kaolinowy LDl5peros mg/kg 58 36 Obrzek karaginowy LD1$ per os mg/kg 69 16.5 Srednia wartosc LD,5 mg/kg 63.5 26.3 Ostra toksycznosc LD$ft mg/kg 864 2000 Wskaznik terapeutyczny Stosunek toksycznego do dzialania LD5t/LDIf 13.6 76 Nowe zwiazki o wzorze ogólnym 1 mozna przerabiac do farmaceutycznego stosowania ewentualnie w polaczeniu z innymi substancjami czynnymi o wzorze ogólnymi, na zwykle uzywane preparaty. Dawka jednostkowa wynosi 50-400 mg, korzystnie 100-300 mg, dawka dzienna wynosi 100—1000 mg, korzystnie' 150-600 mg.Przyklad I. Amid kwasu 3-(2'-f luoro-4-bifenylilo)-2-propenokarboksylowego.Do zawiesiny 19,2 g (0,075 mola) kwasu trans-3-(2'-fluoro-4-bifenylilo)-2-propenokarboksylowego (temperatura topnienia 177°C) w 200 ml absolutnego benzenu dodaje sie 13,3 g (0,1125 mola) chlorku tionylu, ogrzewa przez 2 godziny pod chlodnica zwrotna, oddestylowuje rozpuszczalnik i nadmiar chlorku tionylu.Krystaliczna pozostalosc chlorku kwasowego rozpuszcza sie w 200 ml bezwodnego 1,2-dwumetoksyetanu iwkrapla podczas mieszania i oziebia 200 ml 1,2-dwumetoksyetanu nasyconego gazowym amoniakiem. Po zakonczeniu dodawania miesza sie w temperaturze pokojowej jeszcze przez 1 godzine, mieszanine reakcyjna wprowadza sie do okolo 1 I wody z Jodem i odsacza wytracony osad. Otrzymuje sie bezbarwny amid kwasu 3-(2'- -f Iuoro-4-bifeny I ilo)-2-propenokarboksylowego- o temperaturze topnienia 168—170°C (z ukladu aceton/octan etylenu/ z wydajnoscia 9,5 g (49,7% wydajnosci teoretycznej).Przyklad II. Amid kwasu 3-(2'-fluoro-4-bifenylilo)-2-propenokarboksylowego.Roztwór 8,2 g estru etylowego kwasu 3-(2'-fluoro-4-bifenylilo)-2-propenokarboksylowego (temperatura topnienia 53°C) w 100 ml metanolu zadaje sie 200 ml nasyconego amoniakiem metanolu podczas mieszania.Pozostawia sie przez 1 godzine w temperaturze pokojowej i ogrzewa przez godzine pod chlodnica zwrotna.Roztwór odparowuje sie i pozostalosc przekrystaliz^wuje dwa razy z ukladu aceton/octan etylu. Wydajnosc: 3,2 g (41% wydajnosci teoretycznej). Temperatura topnienia: 168-170°C.Ten sam zwiazek otrzymuje sie z podobna wydajnoscia z estru metylowego kwasu 3-(2'-fluoro-4-bifenylilo)-2-propenokarboksylowego. PL
Claims (2)
- Zastrzezenia patentowe 1. Sposób wytwarzania nowych amidów kwasu 3-(4-bifenylilo)-2-propenokarboksylowego o wzorze ogólnym 1, w którym Ri oznacza atom fluoru lub chloru, znamienny tym, ze ester lub halogenek kwasu 3 -(4-bifenylilo)-2-propenokarboksylowego o wzorze ogólnym 2, w którym Rx ma wyzej podane znaczenie, a X oznacza grupe alkoksylowa lub atom chlorowca, wprowadza sie w reakcje z amoniakiem.94510 3
- 2. Sposób wedlug zastrz. 1,znamienny tym, ze reakcje prowadzi sie w rozpuszczalniku. WZCSR 1 R' CK, o / W W_CH-c'-X WZÓR 2 PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2240441A DE2240441A1 (de) | 1972-08-17 | 1972-08-17 | Neue biphenylderivate und verfahren zur herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL94510B1 true PL94510B1 (pl) | 1977-08-31 |
Family
ID=5853790
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973186474A PL94510B1 (pl) | 1972-08-17 | 1973-08-16 | Sposob wytwarzania nowych amidow kwasu 3-(4-bifenylilo)-2-propenokarboksylowego |
| PL1973164708A PL90397B1 (pl) | 1972-08-17 | 1973-08-16 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973164708A PL90397B1 (pl) | 1972-08-17 | 1973-08-16 |
Country Status (19)
| Country | Link |
|---|---|
| JP (2) | JPS49124052A (pl) |
| AT (3) | AT323144B (pl) |
| AU (2) | AU5930873A (pl) |
| BE (3) | BE803732A (pl) |
| BG (3) | BG21197A3 (pl) |
| CH (1) | CH588435A5 (pl) |
| CS (3) | CS165385B2 (pl) |
| DD (2) | DD107901A5 (pl) |
| DE (1) | DE2240441A1 (pl) |
| ES (4) | ES417883A1 (pl) |
| FR (2) | FR2196168B1 (pl) |
| GB (2) | GB1411495A (pl) |
| HU (2) | HU166516B (pl) |
| IL (2) | IL43003A0 (pl) |
| NL (2) | NL7311301A (pl) |
| PL (2) | PL94510B1 (pl) |
| RO (2) | RO62918A (pl) |
| SU (11) | SU482039A3 (pl) |
| ZA (3) | ZA735629B (pl) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2457275A1 (fr) * | 1979-05-21 | 1980-12-19 | Fabre Sa Pierre | Acides p-biphenyl-4 methyl-2 buten-3 oiques utiles dans le traitement des rhumatismes |
| RU2686489C1 (ru) * | 2018-12-27 | 2019-04-29 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный университет (СПбГУ)" | Способ получения α-диазокарбонильных соединений в водной среде |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2162038A1 (de) * | 1970-05-05 | 1972-08-17 | William H Rorer Ine , Fort Washington, Pa (V St A ) | Verfahren zur Herstellung von synthe tischen Alkansauren und deren Derivaten |
| BE776316R (fr) * | 1971-03-10 | 1972-06-06 | Rorer Inc William H | Nouveaux derives d'acides phenyl-acetiques substitues et procede pour leur |
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1972
- 1972-08-17 DE DE2240441A patent/DE2240441A1/de active Pending
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1973
- 1973-08-14 AT AT710873A patent/AT323144B/de not_active IP Right Cessation
- 1973-08-14 CH CH1170773A patent/CH588435A5/xx not_active IP Right Cessation
- 1973-08-14 ES ES417883A patent/ES417883A1/es not_active Expired
- 1973-08-14 AT AT710773A patent/AT323143B/de not_active IP Right Cessation
- 1973-08-14 AT AT711273A patent/AT328427B/de not_active IP Right Cessation
- 1973-08-14 ES ES417884A patent/ES417884A1/es not_active Expired
- 1973-08-15 HU HUTO925A patent/HU166516B/hu unknown
- 1973-08-15 SU SU1958291A patent/SU482039A3/ru active
- 1973-08-15 SU SU1958288A patent/SU484679A3/ru active
- 1973-08-15 BG BG24327A patent/BG21197A3/xx unknown
- 1973-08-15 BG BG24328A patent/BG22069A3/xx not_active Expired
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- 1973-08-15 SU SU1958290A patent/SU511846A3/ru active
- 1973-08-15 HU HUTO926A patent/HU166517B/hu unknown
- 1973-08-15 DD DD172906A patent/DD108071A5/xx unknown
- 1973-08-16 NL NL7311301A patent/NL7311301A/xx unknown
- 1973-08-16 PL PL1973186474A patent/PL94510B1/pl unknown
- 1973-08-16 ZA ZA00735629A patent/ZA735629B/xx unknown
- 1973-08-16 ZA ZA00735628A patent/ZA735628B/xx unknown
- 1973-08-16 CS CS5793A patent/CS165385B2/cs unknown
- 1973-08-16 JP JP48092053A patent/JPS49124052A/ja active Pending
- 1973-08-16 ZA ZA00735616A patent/ZA735616B/xx unknown
- 1973-08-16 CS CS4904A patent/CS165387B2/cs unknown
- 1973-08-16 JP JP48092052A patent/JPS49124051A/ja active Pending
- 1973-08-16 PL PL1973164708A patent/PL90397B1/pl unknown
- 1973-08-16 GB GB3884373A patent/GB1411495A/en not_active Expired
- 1973-08-16 GB GB3884473A patent/GB1410852A/en not_active Expired
- 1973-08-16 NL NL7311300A patent/NL7311300A/xx unknown
- 1973-08-16 AU AU59308/73A patent/AU5930873A/en not_active Expired
- 1973-08-16 AU AU59309/73A patent/AU476340B2/en not_active Expired
- 1973-08-16 IL IL43003A patent/IL43003A0/xx unknown
- 1973-08-16 IL IL43004A patent/IL43004A0/xx unknown
- 1973-08-16 CS CS4903A patent/CS165386B2/cs unknown
- 1973-08-17 FR FR7330076A patent/FR2196168B1/fr not_active Expired
- 1973-08-17 FR FR7330075A patent/FR2196167B1/fr not_active Expired
- 1973-08-17 RO RO7300075822A patent/RO62918A/ro unknown
- 1973-08-17 BE BE134689A patent/BE803732A/xx unknown
- 1973-08-17 RO RO7300075821A patent/RO62917A/ro unknown
- 1973-08-17 BE BE134691A patent/BE803734A/xx unknown
- 1973-08-17 BE BE134690A patent/BE803733A/xx unknown
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1974
- 1974-10-21 SU SU2069771A patent/SU520030A3/ru active
- 1974-10-21 SU SU2069774A patent/SU552021A3/ru active
- 1974-10-21 SU SU2069577A patent/SU520907A3/ru active
- 1974-10-21 SU SU2069578A patent/SU511847A3/ru active
- 1974-10-21 SU SU7402069575A patent/SU577967A3/ru active
- 1974-10-21 SU SU2069114A patent/SU538658A3/ru active
- 1974-10-21 SU SU2069110A patent/SU554810A3/ru active
- 1974-10-21 SU SU2069576A patent/SU561505A3/ru active
- 1974-11-30 ES ES432464A patent/ES432464A1/es not_active Expired
- 1974-11-30 ES ES432465A patent/ES432465A1/es not_active Expired
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