CA1118448A - Compositions renfermant du cis-2-benzoyl-3-hydroxy- crotononitrile, et methode d'utilisation pour traiter les inflammations et les troubles articulatoires - Google Patents

Compositions renfermant du cis-2-benzoyl-3-hydroxy- crotononitrile, et methode d'utilisation pour traiter les inflammations et les troubles articulatoires

Info

Publication number: CA1118448A
Authority: CA; Canada
Prior art keywords: benzoyl; hydroxy; cis; salt; hydrogen
Prior art date: 1978-03-31
Legal status (The legal status 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 status listed.): Expired

Application number

CA000304830A

Other languages

English (en)

Inventor

John W. Hanifin

David N. Ridge

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

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.)

1978-03-31

Filing date

1978-06-06

Publication date

1982-02-16

1978-03-31 Priority claimed from US05/892,002 external-priority patent/US4170656A/en

1978-06-06 Application filed by Individual filed Critical Individual

1982-02-16 Application granted granted Critical

1982-02-16 Publication of CA1118448A publication Critical patent/CA1118448A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 42
238000000034 method Methods 0.000 title claims abstract description 27
230000006866 deterioration Effects 0.000 title abstract description 9
206010061218 Inflammation Diseases 0.000 title abstract description 6
230000004054 inflammatory process Effects 0.000 title abstract description 6
150000001875 compounds Chemical class 0.000 claims description 43
ZJRCIQAMTAINCB-UHFFFAOYSA-N benzoylacetonitrile Chemical compound N#CCC(=O)C1=CC=CC=C1 ZJRCIQAMTAINCB-UHFFFAOYSA-N 0.000 claims description 24
-1 benzoylacetonitrile anion Chemical class 0.000 claims description 17
ZLUSCZLCHQSJRU-UHFFFAOYSA-N thallium(1+) Chemical class [Tl+] ZLUSCZLCHQSJRU-UHFFFAOYSA-N 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
159000000000 sodium salts Chemical class 0.000 claims description 10
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
150000001266 acyl halides Chemical class 0.000 claims description 7
150000001768 cations Chemical class 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
238000009833 condensation Methods 0.000 claims description 5
230000005494 condensation Effects 0.000 claims description 5
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
YCKLUMSAXJBBQB-UHFFFAOYSA-N 2-methylbutanoyl fluoride Chemical compound CCC(C)C(F)=O YCKLUMSAXJBBQB-UHFFFAOYSA-N 0.000 claims description 3
KOYWUYIBEXFRFH-UHFFFAOYSA-N 3-oxopentanenitrile Chemical compound CCC(=O)CC#N KOYWUYIBEXFRFH-UHFFFAOYSA-N 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
230000010933 acylation Effects 0.000 claims description 3
238000005917 acylation reaction Methods 0.000 claims description 3
GSJWYIDMIRQHMV-UHFFFAOYSA-N butanoyl fluoride Chemical compound CCCC(F)=O GSJWYIDMIRQHMV-UHFFFAOYSA-N 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims description 2
KSGGIONYAUAWPY-UHFFFAOYSA-N pentanoyl fluoride Chemical compound CCCCC(F)=O KSGGIONYAUAWPY-UHFFFAOYSA-N 0.000 claims description 2
WMFABESKCHGSRC-UHFFFAOYSA-N propanoyl fluoride Chemical compound CCC(F)=O WMFABESKCHGSRC-UHFFFAOYSA-N 0.000 claims description 2
239000000126 substance Substances 0.000 claims 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
FSQOYWQCIXSBNP-UHFFFAOYSA-N 2-methylpropanoyl fluoride Chemical compound CC(C)C(F)=O FSQOYWQCIXSBNP-UHFFFAOYSA-N 0.000 claims 1
KVFKXDPQHYKWAD-UHFFFAOYSA-N 3-methylbutanoyl fluoride Chemical compound CC(C)CC(F)=O KVFKXDPQHYKWAD-UHFFFAOYSA-N 0.000 claims 1
FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
150000002905 orthoesters Chemical class 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 5
229940121363 anti-inflammatory agent Drugs 0.000 abstract description 5
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125000002091 cationic group Chemical group 0.000 abstract description 4
241000124008 Mammalia Species 0.000 abstract description 3
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230000002401 inhibitory effect Effects 0.000 abstract description 3
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
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239000000243 solution Substances 0.000 description 25
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
239000002244 precipitate Substances 0.000 description 13
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 11
241000700159 Rattus Species 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000000725 suspension Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
238000012360 testing method Methods 0.000 description 9
229960001701 chloroform Drugs 0.000 description 7
AOMUALOCHQKUCD-UHFFFAOYSA-N dodecyl 4-chloro-3-[[3-(4-methoxyphenyl)-3-oxopropanoyl]amino]benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=C(Cl)C(NC(=O)CC(=O)C=2C=CC(OC)=CC=2)=C1 AOMUALOCHQKUCD-UHFFFAOYSA-N 0.000 description 7
238000001914 filtration Methods 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
238000000746 purification Methods 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
229920002261 Corn starch Polymers 0.000 description 6
206010015150 Erythema Diseases 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
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 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
239000008120 corn starch Substances 0.000 description 6
231100000321 erythema Toxicity 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
239000012071 phase Substances 0.000 description 6
206010003246 arthritis Diseases 0.000 description 5
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239000011541 reaction mixture Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000003981 vehicle Substances 0.000 description 5
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
206010030113 Oedema Diseases 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
206010042674 Swelling Diseases 0.000 description 4
235000019445 benzyl alcohol Nutrition 0.000 description 4
230000037396 body weight Effects 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
235000010418 carrageenan Nutrition 0.000 description 4
229920001525 carrageenan Polymers 0.000 description 4
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238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
229940091249 fluoride supplement Drugs 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
239000000600 sorbitol Substances 0.000 description 4
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239000008215 water for injection Substances 0.000 description 4
GAWMEALSAGEDJR-UHFFFAOYSA-N 1-(5-phenyl-1,2-oxazol-4-yl)ethanone Chemical compound C1=NOC(C=2C=CC=CC=2)=C1C(=O)C GAWMEALSAGEDJR-UHFFFAOYSA-N 0.000 description 3
OPXYNEYEDHAXOM-UHFFFAOYSA-N 3-oxobutanenitrile Chemical compound CC(=O)CC#N OPXYNEYEDHAXOM-UHFFFAOYSA-N 0.000 description 3
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241000700198 Cavia Species 0.000 description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
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RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
YLGWBYPRALKBCK-UHFFFAOYSA-N (5-methyl-1,2-oxazol-4-yl)-phenylmethanone Chemical compound O1N=CC(C(=O)C=2C=CC=CC=2)=C1C YLGWBYPRALKBCK-UHFFFAOYSA-N 0.000 description 2
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GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
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JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
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DZFYOYRNBGNPJW-UHFFFAOYSA-N ethoxythallium Chemical compound [Tl+].CC[O-] DZFYOYRNBGNPJW-UHFFFAOYSA-N 0.000 description 2
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CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 2
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235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
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CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
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239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
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239000004299 sodium benzoate Substances 0.000 description 2
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229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
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239000008107 starch Substances 0.000 description 2
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
CULOEOTWMUCRSJ-UHFFFAOYSA-M thallium(i) fluoride Chemical compound [Tl]F CULOEOTWMUCRSJ-UHFFFAOYSA-M 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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Landscapes

Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA000304830A 1978-03-31 1978-06-06 Compositions renfermant du cis-2-benzoyl-3-hydroxy- crotononitrile, et methode d'utilisation pour traiter les inflammations et les troubles articulatoires Expired CA1118448A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US892,002		1978-03-31
US05/892,002 US4170656A (en)	1977-05-31	1978-03-31	Compositions containing cis-2-benzoyl-3-hydroxy-crotononitrile used to treat inflammation and joint deterioration

Publications (1)

Publication Number	Publication Date
CA1118448A true CA1118448A (fr)	1982-02-16

Family

ID=25399199

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000304830A Expired CA1118448A (fr)	1978-03-31	1978-06-06	Compositions renfermant du cis-2-benzoyl-3-hydroxy- crotononitrile, et methode d'utilisation pour traiter les inflammations et les troubles articulatoires

Country Status (1)

Country	Link
CA (1)	CA1118448A (fr)

1978
- 1978-06-06 CA CA000304830A patent/CA1118448A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-02-16	MKEX	Expiry

Publication	Publication Date	Title
CA2118859C (fr)	2004-07-13	Enantiomeres de 1-[(4-chlorophenyl)phenylmethyl]-4- [(4-methylphenyl)sulfonyl] piperazine
DK167759B1 (da)	1993-12-13	Thiazol-derivater til anvendelse som mellemprodukter
US4173650A (en)	1979-11-06	Cis-2-benzoyl-3-hydroxy-2-alkenonitriles as anti-inflammatory agents
US4174397A (en)	1979-11-13	Thiazolidine derivatives
NO170883B (no)	1992-09-14	Fremgangsmaate for fremstilling av 2-amino-5-hydroksy-4-metylpyrimidin-derivater
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