CA1169776A - Derives anti-inflammatoires de l'acide phenylacetique en usage topique - Google Patents

Derives anti-inflammatoires de l'acide phenylacetique en usage topique

Info

Publication number: CA1169776A
Authority: CA; Canada
Prior art keywords: compound; formula; composition; acceptable salt; phenyl
Prior art date: 1980-06-09
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

CA000379199A

Other languages

English (en)

Inventor

Atsusuke Terada

Eiichi Misaka

Kazue Hasegawa

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.)

Sankyo Co Ltd

Original Assignee

Sankyo Co Ltd

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.)

1980-06-09

Filing date

1981-06-08

Publication date

1984-06-26

1980-06-09 Priority claimed from JP7732180A external-priority patent/JPS574919A/ja

1980-10-17 Priority claimed from JP14525180A external-priority patent/JPS5770867A/ja

1981-06-08 Application filed by Sankyo Co Ltd filed Critical Sankyo Co Ltd

1984-06-26 Application granted granted Critical

1984-06-26 Publication of CA1169776A publication Critical patent/CA1169776A/fr

Status Expired legal-status Critical Current

Links

230000003110 anti-inflammatory effect Effects 0.000 title claims description 8
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 47
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
239000000203 mixture Substances 0.000 claims description 33
-1 amine salt Chemical class 0.000 claims description 14
239000002674 ointment Substances 0.000 claims description 10
239000004264 Petrolatum Substances 0.000 claims description 9
229940066842 petrolatum Drugs 0.000 claims description 9
235000019271 petrolatum Nutrition 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
239000000839 emulsion Substances 0.000 claims description 8
239000003755 preservative agent Substances 0.000 claims description 8
239000003921 oil Substances 0.000 claims description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
239000004615 ingredient Substances 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 4
230000000699 topical effect Effects 0.000 claims description 4
239000001993 wax Substances 0.000 claims description 4
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 3
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235000014113 dietary fatty acids Nutrition 0.000 claims description 3
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150000004665 fatty acids Chemical class 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
239000006210 lotion Substances 0.000 claims description 3
241001465754 Metazoa Species 0.000 claims description 2
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239000002270 dispersing agent Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
239000003974 emollient agent Substances 0.000 claims description 2
239000003995 emulsifying agent Substances 0.000 claims description 2
239000003925 fat Substances 0.000 claims description 2
150000002191 fatty alcohols Chemical class 0.000 claims description 2
239000003349 gelling agent Substances 0.000 claims description 2
125000005456 glyceride group Chemical group 0.000 claims description 2
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239000003381 stabilizer Substances 0.000 claims description 2
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229940121363 anti-inflammatory agent Drugs 0.000 abstract description 7
239000002260 anti-inflammatory agent Substances 0.000 abstract description 7
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 abstract description 7
125000003710 aryl alkyl group Chemical group 0.000 abstract description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
238000004821 distillation Methods 0.000 description 11
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 9
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VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 8
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238000006243 chemical reaction Methods 0.000 description 8
238000000034 method Methods 0.000 description 8
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 8
YMBXTVYHTMGZDW-UHFFFAOYSA-N loxoprofen Chemical compound C1=CC(C(C(O)=O)C)=CC=C1CC1C(=O)CCC1 YMBXTVYHTMGZDW-UHFFFAOYSA-N 0.000 description 7
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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238000004458 analytical method Methods 0.000 description 6
238000001816 cooling Methods 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
238000001819 mass spectrum Methods 0.000 description 6
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
229960000541 cetyl alcohol Drugs 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
235000010446 mineral oil Nutrition 0.000 description 5
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000002585 base Substances 0.000 description 4
235000013871 bee wax Nutrition 0.000 description 4
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000009472 formulation Methods 0.000 description 4
229940075507 glyceryl monostearate Drugs 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
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 4
229940057995 liquid paraffin Drugs 0.000 description 4
229960003511 macrogol Drugs 0.000 description 4
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 4
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 4
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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229910000029 sodium carbonate Inorganic materials 0.000 description 4
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235000011152 sodium sulphate Nutrition 0.000 description 4
229960005078 sorbitan sesquioleate Drugs 0.000 description 4
AUZUGWXLBGZUPP-UHFFFAOYSA-N 2-[4-[(2-oxocyclohexylidene)methyl]phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C=C1C(=O)CCCC1 AUZUGWXLBGZUPP-UHFFFAOYSA-N 0.000 description 3
125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 3
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000004475 Arginine Substances 0.000 description 3
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
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229920001214 Polysorbate 60 Polymers 0.000 description 3
235000021355 Stearic acid Nutrition 0.000 description 3
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 3
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229960002216 methylparaben Drugs 0.000 description 3
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
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229940126062 Compound A Drugs 0.000 description 2
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QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
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230000004054 inflammatory process Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
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150000007530 organic bases Chemical class 0.000 description 1
239000002540 palm oil Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 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
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000000473 propyl gallate Substances 0.000 description 1
229940075579 propyl gallate Drugs 0.000 description 1
235000010388 propyl gallate Nutrition 0.000 description 1
239000008213 purified water Substances 0.000 description 1
FXDIJNSVKPLQHV-UHFFFAOYSA-N pyridin-4-ylmethyl 2-[4-[(2-oxocyclopentyl)methyl]phenyl]propanoate Chemical compound O=C1C(CCC1)CC1=CC=C(C=C1)C(C(=O)OCC1=CC=NC=C1)C FXDIJNSVKPLQHV-UHFFFAOYSA-N 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
150000003872 salicylic acid derivatives Chemical class 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000004328 sodium tetraborate Substances 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
OABCNCKSXCXGOH-UHFFFAOYSA-M sodium;2-[4-[(2-oxocyclohexylidene)methyl]phenyl]propanoate Chemical compound [Na+].C1=CC(C(C([O-])=O)C)=CC=C1C=C1C(=O)CCCC1 OABCNCKSXCXGOH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000012177 spermaceti Substances 0.000 description 1
229940084106 spermaceti Drugs 0.000 description 1
229940032094 squalane Drugs 0.000 description 1
229940031439 squalene Drugs 0.000 description 1
TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
229940012831 stearyl alcohol Drugs 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/86—Unsaturated compounds containing keto groups containing six-membered aromatic rings and other rings

CA000379199A 1980-06-09 1981-06-08 Derives anti-inflammatoires de l'acide phenylacetique en usage topique Expired CA1169776A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP77321/80		1980-06-09
JP7732180A JPS574919A (en)	1980-06-09	1980-06-09	Anti-inflammatory for external use
JP145251/80		1980-10-17
JP14525180A JPS5770867A (en)	1980-10-17	1980-10-17	Phenylacetic ester derivative

Publications (1)

Publication Number	Publication Date
CA1169776A true CA1169776A (fr)	1984-06-26

Family

ID=26418416

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000379199A Expired CA1169776A (fr)	1980-06-09	1981-06-08	Derives anti-inflammatoires de l'acide phenylacetique en usage topique

Country Status (8)

Country	Link
CA (1)	CA1169776A (fr)
CH (1)	CH645539A5 (fr)
DE (1)	DE3122791A1 (fr)
FR (1)	FR2483918B1 (fr)
GB (1)	GB2078732B (fr)
IT (1)	IT1193734B (fr)
NL (1)	NL192371C (fr)
SE (1)	SE8103598L (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6038323A (ja) *	1983-08-10	1985-02-27	Sankyo Co Ltd	眼科用消炎剤
US5620980A (en) *	1995-02-22	1997-04-15	Macrochem Corporation	Method for treating hair loss
CN109020808B (zh) *	2017-06-12	2021-07-06	浙江九洲药业股份有限公司	一种取代苯乙酸衍生物的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4161538A (en) *	1977-04-05	1979-07-17	Sankyo Company Limited	Substituted phenylacetic acid derivatives and process for the preparation thereof
JPS5432460A (en) *	1977-08-16	1979-03-09	Sankyo Co Ltd	Cycloalkylidenemethylphenylacetic acid derivative and their preparation
DE2804051A1 (de) *	1978-01-27	1979-08-09	Schering Ag	Neue phenylessigsaeure-derivate
DD141422A5 (de) *	1978-01-27	1980-04-30	Schering Ag	Verfahren zur herstellung von phenylessigsaeure-derivaten

1981
- 1981-06-03 CH CH364581A patent/CH645539A5/de not_active IP Right Cessation
- 1981-06-08 CA CA000379199A patent/CA1169776A/fr not_active Expired
- 1981-06-08 IT IT67784/81A patent/IT1193734B/it active
- 1981-06-09 FR FR8111293A patent/FR2483918B1/fr not_active Expired
- 1981-06-09 DE DE19813122791 patent/DE3122791A1/de active Granted
- 1981-06-09 GB GB8117684A patent/GB2078732B/en not_active Expired
- 1981-06-09 SE SE8103598A patent/SE8103598L/xx not_active Application Discontinuation
- 1981-06-09 NL NL8102775A patent/NL192371C/nl not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB2078732B (en)	1984-02-15
NL192371C (nl)	1997-07-04
FR2483918B1 (fr)	1988-05-27
SE8103598L (sv)	1981-12-10
CH645539A5 (de)	1984-10-15
FR2483918A1 (fr)	1981-12-11
IT8167784A0 (it)	1981-06-08
NL8102775A (nl)	1982-01-04
DE3122791C2 (fr)	1992-08-13
DE3122791A1 (de)	1982-05-06
NL192371B (nl)	1997-03-03
IT1193734B (it)	1988-08-24
GB2078732A (en)	1982-01-13

Legal Events

Date	Code	Title	Description
2001-06-26	MKEX	Expiry

Publication	Publication Date	Title
US4551475A (en)	1985-11-05	Pharmaceutical preparations for topical application which contain salts of alkanecarboxylic acids
FI87454B (fi)	1992-09-30	Polycykliska aromatiska derivat, deras framstaellningsfoerfarande och tillaempning inom kosmetik.
US3950418A (en)	1976-04-13	Vitamin A acid amides
EP0002341B1 (fr)	1982-01-20	Complexes de cuivre bivalent, procédé pour leur préparation et compositions les contenant
US4287190A (en)	1981-09-01	Complexes of bivalent copper
EP0094599A1 (fr)	1983-11-23	Utilisation de dérivés de l'acide aminophenylacétique pour la préparation d'un médicament immunomodulant
KR870001917B1 (ko)	1987-10-22	피리딜화합물의 제조방법
RU2178787C2 (ru)	2002-01-27	Биароматические соединения и фармацевтические и косметические композиции, включающие их
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