CA1043806A - Phenoxy-alkyl-carboxylic acid derivatives - Google Patents

Phenoxy-alkyl-carboxylic acid derivatives

Info

Publication number: CA1043806A
Authority: CA; Canada
Prior art keywords: ethyl; phenoxy; naphth; formula; methyl
Prior art date: 1974-02-06
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

CA218,899A

Other languages

English (en)

French (fr)

Other versions

CA218899S (fr

Inventor

Hans P. Wolff

Ernst-Christian Witte

Kurt Stach

Harald Stork

Felix H. Schmidt

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.)

Roche Diagnostics GmbH

Original Assignee

Boehringer Mannheim GmbH

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.)

1974-02-06

Filing date

1975-01-29

Publication date

1978-12-05

1975-01-29 Application filed by Boehringer Mannheim GmbH filed Critical Boehringer Mannheim GmbH

1978-12-05 Application granted granted Critical

1978-12-05 Publication of CA1043806A publication Critical patent/CA1043806A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 claims abstract description 49
150000001875 compounds Chemical class 0.000 claims abstract description 48
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 19
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 claims abstract 2
-1 hydroxyamino compound Chemical class 0.000 claims description 57
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 26
239000000126 substance Substances 0.000 claims description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
125000006239 protecting group Chemical group 0.000 claims description 14
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 11
NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 claims description 10
229960003732 tyramine Drugs 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
PLWGVNKMMSGMCW-UHFFFAOYSA-N ethyl 2-[4-[(naphthalene-2-carbonylamino)methyl]phenoxy]acetate Chemical compound C1=C(C=CC2=CC=CC=C12)C(=O)NCC1=CC=C(OCC(=O)OCC)C=C1 PLWGVNKMMSGMCW-UHFFFAOYSA-N 0.000 claims description 6
XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 claims description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
150000007529 inorganic bases Chemical class 0.000 claims description 5
150000007530 organic bases Chemical class 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
230000000903 blocking effect Effects 0.000 claims description 4
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 4
CZFWEWPKYIFXQP-UHFFFAOYSA-N ethyl 2-[4-[(naphthalene-1-carbonylamino)methyl]phenoxy]acetate Chemical compound C1(=CC=CC2=CC=CC=C12)C(=O)NCC1=CC=C(OCC(=O)OCC)C=C1 CZFWEWPKYIFXQP-UHFFFAOYSA-N 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
WNHZFZUMJKMSLB-UHFFFAOYSA-N N-[(4-hydroxyphenyl)methyl]naphthalene-2-carboxamide Chemical compound C1=C(C=CC2=CC=CC=C12)C(=O)NCC1=CC=C(C=C1)O WNHZFZUMJKMSLB-UHFFFAOYSA-N 0.000 claims description 3
DZGWFCGJZKJUFP-UHFFFAOYSA-N Tyramine Natural products NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 claims description 3
XZZWSUAELSBSNA-UHFFFAOYSA-N ethyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(CCN)C=C1 XZZWSUAELSBSNA-UHFFFAOYSA-N 0.000 claims description 3
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims description 3
GNICGVUADRUNFK-UHFFFAOYSA-N n-[2-(4-hydroxyphenyl)ethyl]naphthalene-2-carboxamide Chemical compound C1=CC(O)=CC=C1CCNC(=O)C1=CC=C(C=CC=C2)C2=C1 GNICGVUADRUNFK-UHFFFAOYSA-N 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 2
WSTIHDDJVBVQLK-UHFFFAOYSA-N carboxy naphthalene-1-carboxylate Chemical compound OC(=O)OC(=O)c1cccc2ccccc12 WSTIHDDJVBVQLK-UHFFFAOYSA-N 0.000 claims description 2
MEEXXWXSOPKRTC-UHFFFAOYSA-N ethyl 2-[4-(2-aminoethyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(CCN)C=C1 MEEXXWXSOPKRTC-UHFFFAOYSA-N 0.000 claims description 2
UDKIGIDOSXIQBK-UHFFFAOYSA-N ethyl 2-[4-(aminomethyl)phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(CN)C=C1 UDKIGIDOSXIQBK-UHFFFAOYSA-N 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims 9
STOIQTLUHHHLTR-UHFFFAOYSA-N 2-[4-[(naphthalene-2-carbonylamino)methyl]phenoxy]acetic acid Chemical compound C1=C(C=CC2=CC=CC=C12)C(=O)NCC1=CC=C(OCC(=O)O)C=C1 STOIQTLUHHHLTR-UHFFFAOYSA-N 0.000 claims 2
PVHHSQWHIWIQOI-UHFFFAOYSA-N 2-methyl-2-[4-[(naphthalene-1-carbonylamino)methyl]phenoxy]propanoic acid Chemical compound C1(=CC=CC2=CC=CC=C12)C(=O)NCC1=CC=C(OC(C(=O)O)(C)C)C=C1 PVHHSQWHIWIQOI-UHFFFAOYSA-N 0.000 claims 2
150000005209 naphthoic acids Chemical class 0.000 claims 2
AYCWODLBKTWJQM-UHFFFAOYSA-N 4-(aminomethyl)phenol;hydrochloride Chemical compound Cl.NCC1=CC=C(O)C=C1 AYCWODLBKTWJQM-UHFFFAOYSA-N 0.000 claims 1
XHDMUDYVEIUPRB-UHFFFAOYSA-N ethyl 2-[4-(2-aminoethyl)phenoxy]acetate;hydrochloride Chemical compound Cl.CCOC(=O)COC1=CC=C(CCN)C=C1 XHDMUDYVEIUPRB-UHFFFAOYSA-N 0.000 claims 1
AUBPEEOHUNULEG-UHFFFAOYSA-N ethyl 2-[4-(aminomethyl)phenoxy]acetate;hydrochloride Chemical compound Cl.CCOC(=O)COC1=CC=C(CN)C=C1 AUBPEEOHUNULEG-UHFFFAOYSA-N 0.000 claims 1
IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 claims 1
230000001681 protective effect Effects 0.000 claims 1
DZGWFCGJZKJUFP-UHFFFAOYSA-O tyraminium Chemical compound [NH3+]CCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-O 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 abstract description 3
201000001320 Atherosclerosis Diseases 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000001953 recrystallisation Methods 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
229960001701 chloroform Drugs 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000047 product Substances 0.000 description 6
150000001412 amines Chemical class 0.000 description 5
238000010992 reflux Methods 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000002585 base Substances 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000011734 sodium Substances 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-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
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000007791 liquid phase Substances 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
239000002674 ointment Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000012797 qualification Methods 0.000 description 2
239000012048 reactive intermediate Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000005809 transesterification reaction Methods 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
DVPLHEDOLZCKHJ-UHFFFAOYSA-N 2-phenoxyacetic acid;hydrochloride Chemical compound Cl.OC(=O)COC1=CC=CC=C1 DVPLHEDOLZCKHJ-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 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
229930195725 Mannitol Natural products 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
206010067482 No adverse event Diseases 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
238000003436 Schotten-Baumann reaction Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
HDRXZJPWHTXQRI-BHDTVMLSSA-N diltiazem hydrochloride Chemical compound [Cl-].C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CC[NH+](C)C)C2=CC=CC=C2S1 HDRXZJPWHTXQRI-BHDTVMLSSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
229960001484 edetic acid Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
DJLUGWFUVRDHLO-UHFFFAOYSA-N ethyl 4,5-dimethyl-6-oxo-7-propyl-7,8-dihydrocyclopenta[e][1]benzofuran-2-carboxylate Chemical class O=C1C(CCC)CC2=C1C(C)=C(C)C1=C2C=C(C(=O)OCC)O1 DJLUGWFUVRDHLO-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000007344 nucleophilic reaction Methods 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
125000005543 phthalimide group Chemical group 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/75—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- 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
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA218,899A 1974-02-06 1975-01-29 Phenoxy-alkyl-carboxylic acid derivatives Expired CA1043806A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19742405622 DE2405622A1 (de)	1974-02-06	1974-02-06	Neue phenoxyalkylcarbonsaeurederivate und verfahren zur herstellung derselben

Publications (1)

Publication Number	Publication Date
CA1043806A true CA1043806A (en)	1978-12-05

Family

ID=5906747

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA218,899A Expired CA1043806A (en)	1974-02-06	1975-01-29	Phenoxy-alkyl-carboxylic acid derivatives

Country Status (19)

Country	Link
JP (1)	JPS50108249A (de)
AR (1)	AR203228A1 (de)
AT (1)	AT335439B (de)
BE (1)	BE825176A (de)
CA (1)	CA1043806A (de)
DD (1)	DD120015A5 (de)
DE (1)	DE2405622A1 (de)
DK (1)	DK36575A (de)
ES (1)	ES434446A1 (de)
FI (1)	FI750292A (de)
FR (1)	FR2259597B1 (de)
GB (1)	GB1449586A (de)
HU (1)	HU169491B (de)
IE (1)	IE40585B1 (de)
IL (1)	IL46543A0 (de)
NL (1)	NL7501220A (de)
SE (1)	SE7501083L (de)
SU (1)	SU674670A3 (de)
ZA (1)	ZA75703B (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1812315A1 (de) *	1967-12-28	1969-12-04	Nippon Electric Co	Elektromechanische Schwingungseinrichtung
US4214094A (en)	1977-03-30	1980-07-22	Fujisawa Pharmaceutical Co., Ltd.	Substituted-phenyl substituted-alkyl ethers and the preparation thereof
DE2809377A1 (de) *	1978-03-04	1979-09-13	Boehringer Mannheim Gmbh	Phenoxyalkylcarbonsaeure-derivate, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel
JPS5649906B2 (en) *	1978-05-12	1981-11-25	Boehringer Mannheim Gmbh	Manufacture of alphaa4444chlorobenzoylaminoo ethylphenoxyisoethylacetic acid
US7838542B2 (en) *	2006-06-29	2010-11-23	Kinex Pharmaceuticals, Llc	Bicyclic compositions and methods for modulating a kinase cascade
ES2368460T3 (es) *	2006-10-23	2011-11-17	Pfizer Inc.	Compuestos de fenilmetil biciclocarboxiamida sustituidos.
US9714238B2 (en)	2010-07-02	2017-07-25	Allergan, Inc.	Therapeutic agents for ocular hypertension
WO2012003145A2 (en)	2010-07-02	2012-01-05	Allergan, Inc.	Therapeutic agents for ocular hypertension

1974
- 1974-02-06 DE DE19742405622 patent/DE2405622A1/de not_active Withdrawn
1975
- 1975-01-29 CA CA218,899A patent/CA1043806A/en not_active Expired
- 1975-01-31 SE SE7501083A patent/SE7501083L/xx unknown
- 1975-02-03 IL IL46543A patent/IL46543A0/xx unknown
- 1975-02-03 GB GB448375A patent/GB1449586A/en not_active Expired
- 1975-02-03 FI FI750292A patent/FI750292A/fi not_active Application Discontinuation
- 1975-02-03 DD DD183967A patent/DD120015A5/xx unknown
- 1975-02-03 DK DK36575*#A patent/DK36575A/da unknown
- 1975-02-03 NL NL7501220A patent/NL7501220A/xx unknown
- 1975-02-04 ES ES434446A patent/ES434446A1/es not_active Expired
- 1975-02-04 BE BE153054A patent/BE825176A/xx unknown
- 1975-02-04 ZA ZA00750703A patent/ZA75703B/xx unknown
- 1975-02-05 AT AT85775*#A patent/AT335439B/de not_active IP Right Cessation
- 1975-02-05 IE IE231/75A patent/IE40585B1/xx unknown
- 1975-02-05 FR FR7503585A patent/FR2259597B1/fr not_active Expired
- 1975-02-05 HU HUBO1533A patent/HU169491B/hu unknown
- 1975-02-05 SU SU752104685A patent/SU674670A3/ru active
- 1975-02-06 AR AR257551A patent/AR203228A1/es active
- 1975-02-06 JP JP50015856A patent/JPS50108249A/ja active Pending

Also Published As

Publication number	Publication date
JPS50108249A (de)	1975-08-26
AU7701874A (en)	1976-07-01
HU169491B (de)	1976-12-28
DE2405622A1 (de)	1975-08-14
AT335439B (de)	1977-03-10
FR2259597B1 (de)	1980-01-04
ATA85775A (de)	1976-07-15
SE7501083L (de)	1975-08-07
DD120015A5 (de)	1976-05-20
IL46543A0 (en)	1975-04-25
ES434446A1 (es)	1976-12-16
GB1449586A (en)	1976-09-15
NL7501220A (nl)	1975-08-08
FI750292A (de)	1975-08-07
FR2259597A1 (de)	1975-08-29
IE40585L (en)	1975-08-06
BE825176A (fr)	1975-08-04
DK36575A (de)	1975-10-06
AR203228A1 (es)	1975-08-22
SU674670A3 (ru)	1979-07-15
IE40585B1 (en)	1979-07-04
ZA75703B (en)	1976-02-25

Publication	Publication Date	Title
US4258058A (en)	1981-03-24	Phenoxyalkylcarboxylic acid compounds and thrombocyte-aggregation inhibition
US3781328A (en)	1973-12-25	Phenoxy-alkyl-carboxylic acid compounds
CS238611B2 (en)	1985-12-16	Preparation method of sulphone-amides
US3912756A (en)	1975-10-14	New phenoxyalkyl-carboxylic acid compounds and therapeutic compositions
CA1043806A (en)	1978-12-05	Phenoxy-alkyl-carboxylic acid derivatives
US4225613A (en)	1980-09-30	1H-Pyrrole-1-acetamide compounds and their pharmaceutical compositions
US4151303A (en)	1979-04-24	Phenoxyalkylcarboxylic acid compounds and serum-lipid and triglyceride depressing therapeutic compositions
CA1084523A (en)	1980-08-26	Phenoxyalkylcarboxylic acid derivatives
IE45298B1 (en)	1982-07-28	Hypoliidaemic compositions
US4294851A (en)	1981-10-13	Aminobenzoic acid derivatives
US4889846A (en)	1989-12-26	3-(2,5-disubstituted phenylazo)-4-substituted phenylalkan-1-oic acids and esters thereof and method of treating inflammatory disorders therewith
CA1090366A (en)	1980-11-25	N-substituted aralkylanilines having hypolipidaemic activity
JPS61249951A (ja)	1986-11-07	シクロペンチルエ−テル類、それらの製法および医薬組成物
IE57702B1 (en)	1993-03-10	P-oxybenzoic acid derivatives,methods for preparing them and their use for the preparation of medicaments with hypolipemic activity
CA1090340A (en)	1980-11-25	2-aminomethyl-4,6-dihalogenphenol derivatives and methods for the preparation thereof
US2744916A (en)	1956-05-08	Phenyl-substituted salicylamides
US4205087A (en)	1980-05-27	Acetic acid derivatives
US2906777A (en)	1959-09-29	N-acylated hydroxybenzylamino phenols
IL42353A (en)	1977-08-31	Substituted carbonylaminoalkenylenephenoxy-2-propanolamine derivatives their manufacture and pharmaceutical composittions containing them
US4091095A (en)	1978-05-23	Phosphinyl compounds
US4003932A (en)	1977-01-18	Aminoalkylethers
EP0066254B1 (de)	1987-02-04	Mercaptoaminosäuren, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
US4562287A (en)	1985-12-31	2-(4-Biphenylyl)-4-hexenoic acid and derivatives thereof having anti-inflammatory activity
US3526632A (en)	1970-09-01	Derivatives of bis-(4-biphenylyloxy)acetic acid
US4069338A (en)	1978-01-17	Indole derivatives and process for their preparation