NO844373L - Naftyl- og tetrahydronaftyl-substituert naftoesyre og derivater derav - Google Patents

Naftyl- og tetrahydronaftyl-substituert naftoesyre og derivater derav

Info

Publication number: NO844373L
Authority: NO; Norway
Prior art keywords: patient; tumor growth; compound according; hydrogen; inhibiting
Prior art date: 1983-03-03

Application number

NO844373A

Other languages

English (en)

Norwegian (no)

Inventor

Marcia Ilton Dawson

Peter Duncan Hobbs

Krzysztof Andrezej Derdzinski

Original Assignee

Stanford Res Inst Int

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.)

1983-03-03

Filing date

1984-11-02

Publication date

1984-11-02

1984-11-02 Application filed by Stanford Res Inst Int filed Critical Stanford Res Inst Int

1984-11-02 Publication of NO844373L publication Critical patent/NO844373L/no

Links

125000001624 naphthyl group Chemical group 0.000 title description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 title 1
229910017604 nitric acid Inorganic materials 0.000 title 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 56
229910052739 hydrogen Inorganic materials 0.000 claims description 44
239000001257 hydrogen Substances 0.000 claims description 43
-1 phenoxy, mono-hydroxyphenoxy Chemical group 0.000 claims description 35
230000004614 tumor growth Effects 0.000 claims description 33
238000000034 method Methods 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
241001465754 Metazoa Species 0.000 claims description 27
150000002431 hydrogen Chemical class 0.000 claims description 27
239000003937 drug carrier Substances 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 22
208000017520 skin disease Diseases 0.000 claims description 21
210000002919 epithelial cell Anatomy 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
229910052731 fluorine Inorganic materials 0.000 claims description 15
230000003211 malignant effect Effects 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 13
239000011737 fluorine Substances 0.000 claims description 13
230000002113 chemopreventative effect Effects 0.000 claims description 12
229910052727 yttrium Inorganic materials 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Chemical group 0.000 claims description 6
229910052801 chlorine Chemical group 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
230000001225 therapeutic effect Effects 0.000 claims description 6
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims 32
239000000825 pharmaceutical preparation Substances 0.000 claims 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
125000001309 chloro group Chemical group Cl* 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 69
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
102000052812 Ornithine decarboxylases Human genes 0.000 description 9
108700005126 Ornithine decarboxylases Proteins 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000004809 thin layer chromatography Methods 0.000 description 8
206010028980 Neoplasm Diseases 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
210000003437 trachea Anatomy 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical class OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 6
239000000463 material Substances 0.000 description 6
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
210000003491 skin Anatomy 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
241000699670 Mus sp. Species 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
201000011510 cancer Diseases 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000000284 extract Substances 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
229930002330 retinoic acid Natural products 0.000 description 5
150000004492 retinoid derivatives Chemical class 0.000 description 5
229960001727 tretinoin Drugs 0.000 description 5
NLOOVMVNNNYLFS-UHFFFAOYSA-N 6-bromo-1,1,4,4-tetramethyl-2,3-dihydronaphthalene Chemical compound BrC1=CC=C2C(C)(C)CCC(C)(C)C2=C1 NLOOVMVNNNYLFS-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
230000000694 effects Effects 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
238000004817 gas chromatography Methods 0.000 description 4
239000008187 granular material Substances 0.000 description 4
238000011534 incubation Methods 0.000 description 4
108010075526 keratohyalin Proteins 0.000 description 4
238000005259 measurement Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
102000004169 proteins and genes Human genes 0.000 description 4
108090000623 proteins and genes Proteins 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
UHFICAKXFHFOCN-UHFFFAOYSA-N 6-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C=3C=C4C(C)(C)CCC(C4=CC=3)(C)C)=CC=C21 UHFICAKXFHFOCN-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
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 3
108010076876 Keratins Proteins 0.000 description 3
102000011782 Keratins Human genes 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
230000004071 biological effect Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000012267 brine Substances 0.000 description 3
239000012627 chemopreventive agent Substances 0.000 description 3
229940124443 chemopreventive agent Drugs 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
210000002615 epidermis Anatomy 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000007788 liquid Substances 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
229960003104 ornithine Drugs 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
UZDOTHVVSQOCJO-UHFFFAOYSA-N 1-(6-bromonaphthalen-2-yl)ethanone Chemical compound C1=C(Br)C=CC2=CC(C(=O)C)=CC=C21 UZDOTHVVSQOCJO-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
ONNHBALCPUEXBT-UHFFFAOYSA-N 6-bromo-1,1,4,4,7-pentamethyl-2,3-dihydronaphthalene Chemical compound CC1(C)CCC(C)(C)C2=C1C=C(Br)C(C)=C2 ONNHBALCPUEXBT-UHFFFAOYSA-N 0.000 description 2
WIFNLUBZVRKEHQ-UHFFFAOYSA-N 6-bromo-7-methoxy-1,1,4,4-tetramethyl-2,3-dihydronaphthalene Chemical compound CC1(C)CCC(C)(C)C2=C1C=C(Br)C(OC)=C2 WIFNLUBZVRKEHQ-UHFFFAOYSA-N 0.000 description 2
NPMCAVBMOTZUPD-UHFFFAOYSA-N 6-bromonaphthalene-2-carboxylic acid Chemical class C1=C(Br)C=CC2=CC(C(=O)O)=CC=C21 NPMCAVBMOTZUPD-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
208000002874 Acne Vulgaris Diseases 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
201000004624 Dermatitis Diseases 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
229910004373 HOAc Inorganic materials 0.000 description 2
WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 2
206010054949 Metaplasia Diseases 0.000 description 2
206010000496 acne Diseases 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
NNTDMKYPHDXFJX-UHFFFAOYSA-N ethyl 6-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)naphthalene-2-carboxylate Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C1=CC3=CC=C(C=C3C=C1)C(=O)OCC)=CC=2 NNTDMKYPHDXFJX-UHFFFAOYSA-N 0.000 description 2
FJNDHRWJMFOBCX-UHFFFAOYSA-N ethyl 6-bromonaphthalene-2-carboxylate Chemical compound C1=C(Br)C=CC2=CC(C(=O)OCC)=CC=C21 FJNDHRWJMFOBCX-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
SGRWGISGVDVSJV-UHFFFAOYSA-N hexyl nitrite Chemical compound CCCCCCON=O SGRWGISGVDVSJV-UHFFFAOYSA-N 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
230000006698 induction Effects 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
239000002609 medium Substances 0.000 description 2
230000015689 metaplastic ossification Effects 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
230000002265 prevention Effects 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
238000005406 washing Methods 0.000 description 2
ZDPJODSYNODADV-UHFFFAOYSA-N 1,2,3,4-tetramethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=C(C)C(C)=C21 ZDPJODSYNODADV-UHFFFAOYSA-N 0.000 description 1
ZGONASGBWOJHDD-UHFFFAOYSA-N 1-ethyl-2-nitro-1-nitrosoguanidine Chemical compound CCN(N=O)C(N)=N[N+]([O-])=O ZGONASGBWOJHDD-UHFFFAOYSA-N 0.000 description 1
XKFQSLSAPMCGQS-UHFFFAOYSA-N 1-fluoronaphthalene-2-carboxylic acid Chemical compound C1=CC=CC2=C(F)C(C(=O)O)=CC=C21 XKFQSLSAPMCGQS-UHFFFAOYSA-N 0.000 description 1
HSTAGCWQAIXJQM-UHFFFAOYSA-N 2,5-dichloro-2,5-dimethylhexane Chemical compound CC(C)(Cl)CCC(C)(C)Cl HSTAGCWQAIXJQM-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
IQPHMQHCTKNUCL-HCRPVFJGSA-N 2-[2-[(1e)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hexa-1,3,5-trienyl]phenoxy]oxane Chemical compound C=1C=CC=C(OC2OCCCC2)C=1/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C IQPHMQHCTKNUCL-HCRPVFJGSA-N 0.000 description 1
APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
NNTWECUMTLRLCK-RQHVUCQOSA-N 4-[(1z,3e)-2-methyl-4-(2,6,6-trimethylcyclohexen-1-yl)buta-1,3-dienyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1/C=C(/C)\C=C\C1=C(C)CCCC1(C)C NNTWECUMTLRLCK-RQHVUCQOSA-N 0.000 description 1
VZSBAIYVRPSODH-UHFFFAOYSA-N 4-fluoro-6-(3-methoxy-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=C(F)C2=CC(C3=CC4=C(C(CCC4(C)C)(C)C)C=C3OC)=CC=C21 VZSBAIYVRPSODH-UHFFFAOYSA-N 0.000 description 1
AZBWSUZMELXBMR-UHFFFAOYSA-N 4-fluoro-6-(3-methoxy-5,6,7,8-tetramethylnaphthalen-2-yl)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=C(F)C2=CC(C3=CC4=C(C)C(C)=C(C)C(C)=C4C=C3OC)=CC=C21 AZBWSUZMELXBMR-UHFFFAOYSA-N 0.000 description 1
AMDKYPNODLTUMY-UHFFFAOYSA-N 5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-amine Chemical compound NC1=CC=C2C(C)(C)CCC(C)(C)C2=C1 AMDKYPNODLTUMY-UHFFFAOYSA-N 0.000 description 1
BEPKBFLUJAOCLD-UHFFFAOYSA-N 5-fluoro-6-(3-methoxy-5,6,7,8-tetramethylnaphthalen-2-yl)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=C(F)C(C3=CC4=C(C)C(C)=C(C)C(C)=C4C=C3OC)=CC=C21 BEPKBFLUJAOCLD-UHFFFAOYSA-N 0.000 description 1
CPKOCTPXERQBQS-UHFFFAOYSA-N 5-fluoro-6-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=C(F)C(C=3C=C4C(C)(C)CCC(C4=CC=3)(C)C)=CC=C21 CPKOCTPXERQBQS-UHFFFAOYSA-N 0.000 description 1
QXEGZFKQLNCYSZ-UHFFFAOYSA-N 5-fluoro-6-(5,6,7,8-tetramethylnaphthalen-2-yl)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=C(F)C(C3=CC4=C(C)C(C)=C(C(=C4C=C3)C)C)=CC=C21 QXEGZFKQLNCYSZ-UHFFFAOYSA-N 0.000 description 1
CHMUXIOQEWRFBX-UHFFFAOYSA-N 6-(3-chloro-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-5-fluoronaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=C(F)C(C=3C=C4C(C)(C)CCC(C4=CC=3Cl)(C)C)=CC=C21 CHMUXIOQEWRFBX-UHFFFAOYSA-N 0.000 description 1
NSPXENGLSONWCZ-UHFFFAOYSA-N 6-(3-chloro-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C=3C=C4C(C)(C)CCC(C4=CC=3Cl)(C)C)=CC=C21 NSPXENGLSONWCZ-UHFFFAOYSA-N 0.000 description 1
INXLRGPAFGUYBO-UHFFFAOYSA-N 6-(3-methoxy-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC4=C(C(CCC4(C)C)(C)C)C=C3OC)=CC=C21 INXLRGPAFGUYBO-UHFFFAOYSA-N 0.000 description 1
YKIQHZDMJYZTCJ-UHFFFAOYSA-N 6-(5,6,7,8-tetramethylnaphthalen-2-yl)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC4=C(C)C(C)=C(C(=C4C=C3)C)C)=CC=C21 YKIQHZDMJYZTCJ-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/33—Polycyclic acids
- C07C63/337—Polycyclic acids with carboxyl groups bound to condensed ring systems
- C07C63/42—Polycyclic acids with carboxyl groups bound to condensed ring systems containing three or more condensed rings
- C07C63/44—Polycyclic acids with carboxyl groups bound to condensed ring systems containing three or more condensed rings containing one carboxyl group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/33—Polycyclic acids
- C07C63/49—Polycyclic acids containing rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/72—Polycyclic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
- C07C65/26—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic containing rings other than six-membered aromatic rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO844373A 1983-03-03 1984-11-02 Naftyl- og tetrahydronaftyl-substituert naftoesyre og derivater derav NO844373L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/471,744 US4454341A (en)	1983-03-03	1983-03-03	Naphthyl or tetrahydronaphthyl-substituted naphthoic acid and derivatives

Publications (1)

Publication Number	Publication Date
NO844373L true NO844373L (no)	1984-11-02

Family

ID=23872826

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO844373A NO844373L (no)	1983-03-03	1984-11-02	Naftyl- og tetrahydronaftyl-substituert naftoesyre og derivater derav

Country Status (9)

Country	Link
US (1)	US4454341A (da)
EP (1)	EP0137010A4 (da)
JP (1)	JPS60500815A (da)
DE (1)	DE3490104T1 (da)
DK (1)	DK524784A (da)
GB (1)	GB2143824B (da)
NO (1)	NO844373L (da)
SE (1)	SE8405488D0 (da)
WO (1)	WO1984003505A1 (da)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2555571B1 (fr) *	1983-11-28	1986-11-28	Interna Rech Dermatolo Centre	Derives du naphtalene, leur procede de preparation et leur application dans le domaine therapeutique
FR2573755B1 (fr) *	1984-11-27	1988-04-22	Cird	Derives polysubstitues du naphtalene, leur procede de preparation et leur application dans les domaines pharmaceutique et cosmetique
LU85726A1 (fr) *	1985-01-10	1986-08-04	Cird	Nouveaux derives naphtaleniques du benzonorbornene,leur procede de preparation et compositions medicamenteuse et cosmetique les contenant
US4593125A (en) *	1985-03-13	1986-06-03	Celanese Corporation	Acylation of naphthalenes
LU85849A1 (fr) *	1985-04-11	1986-11-05	Cird	Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques
IL80270A0 (en) *	1985-10-11	1987-01-30	Cird	Naphthalene derivatives,their preparation and pharmaceutical compositions containing them
FR2601359B1 (fr) *	1986-07-09	1988-10-28	Cird	Nouveaux derives bicycliques naphtaleniques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire et en cosmetique.
IT1221916B (it) *	1987-03-13	1990-08-23	Blaschim Spa	Metodo migliorato epr acilare un derivato del naftalene
DE3816120A1 (de) *	1988-05-11	1989-11-23	Bayer Ag	Verfahren zur herstellung von unsymmetrischen biarylverbindungen
US5475022A (en) *	1993-10-18	1995-12-12	Allergan, Inc.	Phenyl or heteroaryl and tetrahydronaphthyl substituted diene compounds having retinoid like biological activity
CA2138000A1 (en) *	1994-01-03	1995-07-04	John E. Starrett, Jr.	Retinoid-like compounds
US5648385A (en) *	1994-01-03	1997-07-15	Bristol-Myers Squibb Co.	Retinoid-like compounds
US5559248A (en) *	1995-04-05	1996-09-24	Bristol-Myers Squibb Co.	Retinoid-like heterocycles
US5747542A (en) *	1996-06-21	1998-05-05	Allergan	Oxo-substituted tetrahydronaphthalene derivatives having retinold and/or retinoid antagonist-like biological activity
WO2012056544A1 (ja) *	2010-10-28	2012-05-03	エア・ウォーター株式会社	６－ブロモ－２－ナフタレンカルボン酸精製品の製造方法
WO2014069674A1 (ja) *	2012-11-01	2014-05-08	スガイ化学工業株式会社	６－ブロモ－２－ナフトエ酸の製造方法
EP3152190B1 (en)	2014-06-04	2024-07-31	Haro Pharmaceutical Inc.	18-20 member bi-polycyclic compounds
WO2016105547A1 (en)	2014-12-24	2016-06-30	Concert Pharmaceuticals, Inc.	Deuterated dasabuvir

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3896157A (en) *	1967-01-13	1975-07-22	Syntex Corp	Dihydo 2-naphthylacetic acid derivatives
US3821253A (en) *	1969-04-09	1974-06-28	Syntex Corp	Naphthyl acetaldehyde derivatives;methods of use thereof;and processes for the preparation thereof
US4326055A (en) *	1977-12-22	1982-04-20	Hoffmann-La Roche Inc.	Stilbene derivatives
FR2416214A1 (fr) *	1978-02-02	1979-08-31	Inst Rech Scient Irs	Derives d'acide naphtyl-1 acetique, leur procede de preparation et leur application therapeutique

1983
- 1983-03-03 US US06/471,744 patent/US4454341A/en not_active Expired - Fee Related
1984
- 1984-01-16 JP JP59500830A patent/JPS60500815A/ja active Pending
- 1984-01-16 EP EP19840900792 patent/EP0137010A4/en not_active Withdrawn
- 1984-01-16 GB GB08424775A patent/GB2143824B/en not_active Expired
- 1984-01-16 WO PCT/US1984/000067 patent/WO1984003505A1/en not_active Ceased
- 1984-01-16 DE DE19843490104 patent/DE3490104T1/de not_active Withdrawn
- 1984-11-01 SE SE8405488A patent/SE8405488D0/xx not_active Application Discontinuation
- 1984-11-02 DK DK524784A patent/DK524784A/da not_active Application Discontinuation
- 1984-11-02 NO NO844373A patent/NO844373L/no unknown

Also Published As

Publication number	Publication date
EP0137010A1 (en)	1985-04-17
US4454341A (en)	1984-06-12
DK524784D0 (da)	1984-11-02
WO1984003505A1 (en)	1984-09-13
GB2143824B (en)	1986-09-10
GB2143824A (en)	1985-02-20
DK524784A (da)	1984-11-02
GB8424775D0 (en)	1984-11-07
DE3490104T1 (de)	1985-04-04
EP0137010A4 (en)	1985-08-12
JPS60500815A (ja)	1985-05-30
SE8405488L (sv)	1984-11-01
SE8405488D0 (sv)	1984-11-01

Publication	Publication Date	Title
US4454341A (en)	1984-06-12	Naphthyl or tetrahydronaphthyl-substituted naphthoic acid and derivatives
WO1985000806A1 (en)	1985-02-28	Benzonorbornenyl, benzopyranyl and benzothiopyranyl retinoic acid analogues
AU693434B2 (en)	1998-07-02	Therapeutic use of compounds having selective agonist-like activity on RXR retinoid receptors
US5837725A (en)	1998-11-17	Bridged bicyclic aromatic compounds and their use in modulating gene expression of retinoid receptors
US4826984A (en)	1989-05-02	Heteroarotinoid compounds as anticancer agents
EP0909560A2 (en)	1999-04-21	Treatment o tumors with compounds having RXR retinoid receptor agoinst activity
DE69808065T2 (de)	2003-05-22	Trisubstituierte phenyl derivate mit retinoid agonist, antagonist oder inversagonist biologischer aktivität
EP0054924A2 (en)	1982-06-30	Pharmaceutical compounds, their preparation and use
DE60116642T2 (de)	2006-11-09	Verbindungen mit cytochrom p450ra1 hemmenden aktivität
EP0237986B1 (en)	1991-10-02	Flavone carboxylic acid derivatives
NO175714B (no)	1994-08-15	Analogifremgangsmåte for fremstilling av terapeutisk aktive, aromatiske estere
Dawson et al.	1983	Synthesis and pharmacological activity of 6-[(E)-2-(2, 6, 6-trimethyl-1-cyclohexen-1-yl) ethen-1-yl)]-and 6-(1, 2, 3, 4-tetrahydro-1, 1, 4, 4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acids
DE69106545T2 (de)	1995-06-01	Verbesserungen an Leukotrien-Antagonieten.
JPH01301661A (ja)	1989-12-05	新規ピリジル誘導体
DE69525763T2 (de)	2002-10-02	4,6-DI-t-BUTYL-2,3-DIHYDROBENZOTHIOPHENE, DIE LDL OXIDATION HEMMEN
US4456618A (en)	1984-06-26	Naphthenic and heterocyclic retinoic acid analogues
AU576884B2 (en)	1988-09-08	Transdermal delivery of azatadine
DE68920063T2 (de)	1995-05-11	Derivate von Benzoesäure und Verfahren zu deren Herstellung.
US3683091A (en)	1972-08-08	Certain phenanthrene compounds for treatment of acne
US4532343A (en)	1985-07-30	Aromatic retinoic acid analogues
US5204373A (en)	1993-04-20	Farnesylated tetrahydro-naphthalenols as hypolipidemic agents
US4490414A (en)	1984-12-25	Open chain analogues of retinoic acid
WO1995033745A2 (en)	1995-12-14	Novel compounds useful in modulating gene expression of retinoid responsive genes and/or having anti-ap-1 activity
WO1995033745A9 (en)	1996-01-18	Novel compounds useful in modulating gene expression of retinoid responsive genes and/or having anti-ap-1 activity
US4439614A (en)	1984-03-27	5,6-Methano-5,6-dihydroretinoids