IL28364A - 2-amino-substituted 4,5-diphenyloxazoles having an anti-inflammatory activity - Google Patents

2-amino-substituted 4,5-diphenyloxazoles having an anti-inflammatory activity

Info

Publication number: IL28364A
Authority: IL; Israel
Prior art keywords: fact; compounds; preparation; amine group; group
Prior art date: 1966-08-10

Application number

IL28364A

Other languages

English (en)

Original Assignee

Serono Ist Farm

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1966-08-10

Filing date

1967-07-20

Publication date

1972-06-28

1967-07-20 Application filed by Serono Ist Farm filed Critical Serono Ist Farm

1972-06-28 Publication of IL28364A publication Critical patent/IL28364A/en

Links

-1 2-amino-substituted 4,5-diphenyloxazoles Chemical class 0.000 title description 2
230000003110 anti-inflammatory effect Effects 0.000 title 1
238000000034 method Methods 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 3
239000000706 filtrate Substances 0.000 claims description 3
230000002757 inflammatory effect Effects 0.000 claims description 3
230000001154 acute effect Effects 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
239000000203 mixture Substances 0.000 claims description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
238000001914 filtration Methods 0.000 claims 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 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 claims 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
239000002775 capsule Substances 0.000 claims 1
239000004202 carbamide Substances 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
235000013311 vegetables Nutrition 0.000 claims 1
239000000243 solution Substances 0.000 description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
239000008096 xylene Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
206010063560 Excessive granulation tissue Diseases 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
210000003414 extremity Anatomy 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
210000001126 granulation tissue Anatomy 0.000 description 2
210000003141 lower extremity Anatomy 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000006187 pill Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000005303 weighing Methods 0.000 description 2
RXDYOLRABMJTEF-UHFFFAOYSA-N 2-chloro-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Cl)C(=O)C1=CC=CC=C1 RXDYOLRABMJTEF-UHFFFAOYSA-N 0.000 description 1
IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical group C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
241000206575 Chondrus crispus Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000534944 Thia Species 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000012984 antibiotic solution Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000029142 excretion Effects 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000021332 multicellular organism growth Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
ATJFFYVFTNAWJD-OIOBTWANSA-N tin-116 atom Chemical compound [116Sn] ATJFFYVFTNAWJD-OIOBTWANSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 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
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D263/48—Nitrogen atoms not forming part of a nitro radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (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)

IL28364A 1966-08-10 1967-07-20 2-amino-substituted 4,5-diphenyloxazoles having an anti-inflammatory activity IL28364A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT1839066		1966-08-10

Publications (1)

Publication Number	Publication Date
IL28364A true IL28364A (en)	1972-06-28

Family

ID=11152748

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL28364A IL28364A (en)	1966-08-10	1967-07-20	2-amino-substituted 4,5-diphenyloxazoles having an anti-inflammatory activity

Country Status (9)

Country	Link
US (1)	US3557135A (fr)
BE (1)	BE768161Q (fr)
CH (1)	CH506548A (fr)
DE (1)	DE1695284B2 (fr)
ES (1)	ES343995A1 (fr)
FR (1)	FR7043M (fr)
GB (1)	GB1152627A (fr)
GR (1)	GR33985B (fr)
IL (1)	IL28364A (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3895115A (en) *	1974-03-01	1975-07-15	Serono Ist Farm	Method of inhibiting platelet aggregation
IT1099996B (it) *	1978-10-17	1985-09-28	Anic Spa	Derivati del 4,5-difenil-ossazolo 2-ammino o 2-tio sostituiti e procedimento per il loro ottenimento
EP0149884B1 (fr) *	1983-09-09	1992-12-16	Takeda Chemical Industries, Ltd.	Dérivés de 5-pyridyle-1,3-thiazole, leur préparation et utilisation
US5217971A (en) *	1989-01-05	1993-06-08	Fujisawa Pharmaceutical Co., Ltd.	Thiazole compounds and pharmaceutical composition comprising the same
FR2707984B1 (fr) *	1993-07-23	1995-09-01	Adir	Nouvelles pipérazines substituées, leur procédé de préparation et les compositions les contenant.

1967
- 1967-07-14 CH CH1020167A patent/CH506548A/de not_active IP Right Cessation
- 1967-07-17 GR GR670133985A patent/GR33985B/el unknown
- 1967-07-20 IL IL28364A patent/IL28364A/en unknown
- 1967-07-31 GB GB35096/67A patent/GB1152627A/en not_active Expired
- 1967-08-04 FR FR116960A patent/FR7043M/fr not_active Expired
- 1967-08-08 US US659574A patent/US3557135A/en not_active Expired - Lifetime
- 1967-08-09 DE DE1967J0034349 patent/DE1695284B2/de active Granted
- 1967-08-10 ES ES343995A patent/ES343995A1/es not_active Expired
1971
- 1971-06-04 BE BE768161A patent/BE768161Q/fr active

Also Published As

Publication number	Publication date
CH506548A (de)	1971-04-30
FR7043M (fr)	1969-06-16
US3557135A (en)	1971-01-19
DE1695284A1 (de)	1972-02-03
ES343995A1 (es)	1968-12-16
GR33985B (el)	1968-02-29
BE768161Q (fr)	1971-11-03
GB1152627A (en)	1969-05-21
DE1695284B2 (de)	1976-06-10

Publication	Publication Date	Title
US4194045A (en)	1980-03-18	1-(3,3-Diaryl-3-oxadiazolalkyl)-4-phenyl-4-piperidinomethanols and related compounds
CH672127A5 (fr)	1989-10-31
DE2634288B2 (fr)	1979-06-28
DE69810619T2 (de)	2003-09-25	Oral aktive eisen (iii) chelatoren
US4731472A (en)	1988-03-15	(5,6-dichloro-3-oxo-9A-propyl-2,3,9,9A-tetrahydrofluoren-7-yl)alkanoic acids and alkanimidamides
EP0220573B1 (fr)	1991-12-11	Composés hétérocycliques
IL28364A (en)	1972-06-28	2-amino-substituted 4,5-diphenyloxazoles having an anti-inflammatory activity
DE2737738C2 (de)	1987-01-29	3-Amino-thiophen-4-carbonsäuren und deren Derivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Mittel
US4242348A (en)	1980-12-30	Novel basic substituted-alkylidenamino-oxylalkyl-carboxylic-acid esters
US3947475A (en)	1976-03-30	5-Furoyl-2,2,4-trimethyl-1,4-dihydro-1H-1,5-benzodiazepine as an anti-inflammatory agent
EP0087655A1 (fr)	1983-09-07	Procédé pour la préparation d'acémétacine
DE1960910C3 (de)	1979-11-08	Benzylidenamino-oxyalkancarbonsäuren und deren Derivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
DE2263100A1 (de)	1973-07-12	Neue heterozyklische ester von benzopyranopyridinen
DE2535147A1 (de)	1976-02-19	2-thiol-4,5-diphenyloxazol-s-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
US3590041A (en)	1971-06-29	Novel halo-substituted cinnamic acid heterocyclic amides
US3978227A (en)	1976-08-31	5-furoyl-2,2,4-trimethyl-1,4-dihydro-1h-1,5-benzodiazepine as an anti-inflammatory agent
EP0211157B1 (fr)	1991-01-02	Derivés d'isoxazole, procédé de préparation et préparations pharmaceutiques les contenant
NO742091L (fr)	1975-01-20
DE2605824C3 (de)	1981-04-23	N-Acylaniline, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen
US3819705A (en)	1974-06-25	Quaternary salts of tri-(beta-propyloxyethyl)amine derivatives and process for producing same
DE2735458A1 (de)	1978-02-09	Neue imidazolderivate
US2989530A (en)	1961-06-20	Nu-(5-nitro-2-furoyl)-morpholine
DE2016057C3 (de)	1977-08-18	Eckige Klammer auf (Thenyliden (2)- amino)-oxy] -alkylcarbonsäuren, deren Salze und Alkylester, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE2625585C2 (de)	1986-11-13	6-aminomethylierte, 3-oxygenierte Cholest-5-ene, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel
CH677925A5 (fr)	1991-07-15