ZA200203050B - Novel hydronaphtalene compounds, prepared by a rhodium catalyzed ring opening reaction in the presence of phosphine ligand. - Google Patents
Novel hydronaphtalene compounds, prepared by a rhodium catalyzed ring opening reaction in the presence of phosphine ligand. Download PDFInfo
- Publication number
- ZA200203050B ZA200203050B ZA200203050A ZA200203050A ZA200203050B ZA 200203050 B ZA200203050 B ZA 200203050B ZA 200203050 A ZA200203050 A ZA 200203050A ZA 200203050 A ZA200203050 A ZA 200203050A ZA 200203050 B ZA200203050 B ZA 200203050B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- dihydro
- naphthalen
- formula
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 132
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 239000003446 ligand Substances 0.000 title claims abstract description 12
- 229910000073 phosphorus hydride Inorganic materials 0.000 title claims abstract description 12
- 239000010948 rhodium Substances 0.000 title abstract description 6
- 229910052703 rhodium Inorganic materials 0.000 title abstract description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000007142 ring opening reaction Methods 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 72
- ZKPRFGFRFQXTIU-UHFFFAOYSA-N ctk1a3528 Chemical class C1=CC=CC2=C(O3)C=CC3=C21 ZKPRFGFRFQXTIU-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- -1 tert-butyldimethylsiloxy group Chemical group 0.000 claims description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- HTGSBYSSVSBBBO-HZPDHXFCSA-N [(1r,2r)-1-hydroxy-1,2-dihydronaphthalen-2-yl] benzoate Chemical compound O([C@H]1[C@@H](C2=CC=CC=C2C=C1)O)C(=O)C1=CC=CC=C1 HTGSBYSSVSBBBO-HZPDHXFCSA-N 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- NSQXOUQCNRTSSM-JKSUJKDBSA-N n-[(1r,2s)-2-methoxy-1,2-dihydronaphthalen-1-yl]-2-trimethylsilylethanesulfonamide Chemical compound C1=CC=C2[C@@H](NS(=O)(=O)CC[Si](C)(C)C)[C@@H](OC)C=CC2=C1 NSQXOUQCNRTSSM-JKSUJKDBSA-N 0.000 claims description 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 27
- 239000000126 substance Substances 0.000 claims 26
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 21
- 238000004519 manufacturing process Methods 0.000 claims 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 208000030507 AIDS Diseases 0.000 claims 4
- 208000018737 Parkinson disease Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000001041 indolyl group Chemical group 0.000 claims 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- 125000004494 ethyl ester group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical group NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 3
- FBQWNPNKYJGLOV-RTBURBONSA-N (1r,2r)-2-(3,4-dihydro-2h-quinolin-1-yl)-1,2-dihydronaphthalen-1-ol Chemical compound C1CCC2=CC=CC=C2N1[C@H]1[C@H](O)C2=CC=CC=C2C=C1 FBQWNPNKYJGLOV-RTBURBONSA-N 0.000 claims 2
- HAXMSZUGTNSCIJ-IAGOWNOFSA-N (1r,2r)-2-(n-methylanilino)-1,2-dihydronaphthalen-1-ol Chemical compound CN([C@H]1[C@@H](C2=CC=CC=C2C=C1)O)C1=CC=CC=C1 HAXMSZUGTNSCIJ-IAGOWNOFSA-N 0.000 claims 2
- GQGFWPHVWGBHRC-QZTJIDSGSA-N (1r,2r)-2-indol-1-yl-1,2-dihydronaphthalen-1-ol Chemical compound C1=CC2=CC=CC=C2N1[C@H]1[C@H](O)C2=CC=CC=C2C=C1 GQGFWPHVWGBHRC-QZTJIDSGSA-N 0.000 claims 2
- LONWWQFRIDMMGF-HOTGVXAUSA-N (1s,2s)-2-(4-iodophenoxy)-1,2-dihydronaphthalen-1-ol Chemical compound O([C@@H]1[C@H](C2=CC=CC=C2C=C1)O)C1=CC=C(I)C=C1 LONWWQFRIDMMGF-HOTGVXAUSA-N 0.000 claims 2
- GANSKZKLKUWJHT-QWRGUYRKSA-N (1s,2s)-6,7-difluoro-2-methoxy-1,2-dihydronaphthalen-1-ol Chemical compound FC1=C(F)C=C2[C@H](O)[C@@H](OC)C=CC2=C1 GANSKZKLKUWJHT-QWRGUYRKSA-N 0.000 claims 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 2
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 claims 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 2
- SASFZAFXKVHJPR-HZPDHXFCSA-N (1r,2r)-2-(4-bromophenoxy)-1,2-dihydronaphthalen-1-ol Chemical compound O([C@H]1[C@@H](C2=CC=CC=C2C=C1)O)C1=CC=C(Br)C=C1 SASFZAFXKVHJPR-HZPDHXFCSA-N 0.000 claims 1
- KASATEAOBHMTFX-DLBZAZTESA-N (1r,2s)-2-methoxy-n-phenyl-1,2-dihydronaphthalen-1-amine Chemical compound N([C@@H]1C2=CC=CC=C2C=C[C@@H]1OC)C1=CC=CC=C1 KASATEAOBHMTFX-DLBZAZTESA-N 0.000 claims 1
- BLAFSMXCRFQMMZ-LSDHHAIUSA-N (1r,2s)-n-methyl-2-pyrrolidin-1-yl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound N1([C@@H]2[C@@H](C3=CC=CC=C3CC2)NC)CCCC1 BLAFSMXCRFQMMZ-LSDHHAIUSA-N 0.000 claims 1
- PNIWPYSBBBIQJB-QWRGUYRKSA-N (1s,2s)-2-(2,2,2-trifluoroethoxy)-1,2-dihydronaphthalen-1-ol Chemical compound C1=CC=C2[C@H](O)[C@@H](OCC(F)(F)F)C=CC2=C1 PNIWPYSBBBIQJB-QWRGUYRKSA-N 0.000 claims 1
- HZNBNNXKWSXQIE-HOTGVXAUSA-N (1s,2s)-2-(4-chlorophenoxy)-1,2-dihydronaphthalen-1-ol Chemical compound O([C@@H]1[C@H](C2=CC=CC=C2C=C1)O)C1=CC=C(Cl)C=C1 HZNBNNXKWSXQIE-HOTGVXAUSA-N 0.000 claims 1
- NPMPHCGIRCYCSX-HOTGVXAUSA-N (1s,2s)-2-(4-fluorophenoxy)-1,2-dihydronaphthalen-1-ol Chemical compound O([C@@H]1[C@H](C2=CC=CC=C2C=C1)O)C1=CC=C(F)C=C1 NPMPHCGIRCYCSX-HOTGVXAUSA-N 0.000 claims 1
- JJBOFWFPSCJQNM-HOTGVXAUSA-N (1s,2s)-2-(4-nitrophenoxy)-1,2-dihydronaphthalen-1-ol Chemical compound O([C@@H]1[C@H](C2=CC=CC=C2C=C1)O)C1=CC=C([N+]([O-])=O)C=C1 JJBOFWFPSCJQNM-HOTGVXAUSA-N 0.000 claims 1
- RSGMQSWPAOKZRS-QWRGUYRKSA-N (1s,2s)-2-methoxy-1,2-dihydronaphthalen-1-ol Chemical group C1=CC=C2[C@H](O)[C@@H](OC)C=CC2=C1 RSGMQSWPAOKZRS-QWRGUYRKSA-N 0.000 claims 1
- INLGRZNWACCBCI-IRXDYDNUSA-N (1s,2s)-2-phenylmethoxy-1,2-dihydronaphthalen-1-ol Chemical compound O([C@@H]1[C@H](C2=CC=CC=C2C=C1)O)CC1=CC=CC=C1 INLGRZNWACCBCI-IRXDYDNUSA-N 0.000 claims 1
- RPUBRXMLBUNJLQ-STQMWFEESA-N (1s,2s)-2-propan-2-yloxy-1,2-dihydronaphthalen-1-ol Chemical compound C1=CC=C2[C@H](O)[C@@H](OC(C)C)C=CC2=C1 RPUBRXMLBUNJLQ-STQMWFEESA-N 0.000 claims 1
- AFDFCUPVDSNMSC-TVQRCGJNSA-N (1s,2s)-6,7-dibromo-2-methoxy-5,8-dimethyl-1,2-dihydronaphthalen-1-ol Chemical compound BrC1=C(Br)C(C)=C2[C@H](O)[C@@H](OC)C=CC2=C1C AFDFCUPVDSNMSC-TVQRCGJNSA-N 0.000 claims 1
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims 1
- VNSQXWISTNFYFV-UHFFFAOYSA-N 1,3-dioxol-4-ol Chemical compound OC1=COCO1 VNSQXWISTNFYFV-UHFFFAOYSA-N 0.000 claims 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical group COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 claims 1
- ZLTWIJREHQCJJL-UHFFFAOYSA-N 1-trimethylsilylethanol Chemical compound CC(O)[Si](C)(C)C ZLTWIJREHQCJJL-UHFFFAOYSA-N 0.000 claims 1
- HXPAIKLLIIWLPD-HZPDHXFCSA-N 2-[(1r,2r)-1-hydroxy-1,2-dihydronaphthalen-2-yl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1[C@H]1[C@H](O)C2=CC=CC=C2C=C1 HXPAIKLLIIWLPD-HZPDHXFCSA-N 0.000 claims 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 claims 1
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 claims 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims 1
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 claims 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 claims 1
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 claims 1
- TYCMLEXAPFDKNL-FCHUYYIVSA-N 4-methyl-n-[(1r,2s)-2-piperidin-1-yl-1,2-dihydronaphthalen-1-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N[C@@H]1C2=CC=CC=C2C=C[C@@H]1N1CCCCC1 TYCMLEXAPFDKNL-FCHUYYIVSA-N 0.000 claims 1
- UHGROUJFCKFQIY-VQTJNVASSA-N 4-nitro-n-[(1r,2s)-2-pyrrolidin-1-yl-1,2-dihydronaphthalen-1-yl]benzenesulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)N[C@@H]1C2=CC=CC=C2C=C[C@@H]1N1CCCC1 UHGROUJFCKFQIY-VQTJNVASSA-N 0.000 claims 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims 1
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims 1
- PJXUCPHIKOZAAV-UHFFFAOYSA-N O(C1=CC=CC=C1)C1(CC=CC2=CC=CC=C12)O Chemical compound O(C1=CC=CC=C1)C1(CC=CC2=CC=CC=C12)O PJXUCPHIKOZAAV-UHFFFAOYSA-N 0.000 claims 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims 1
- RYDUJHSMAWBEJS-VXGBXAGGSA-N [(1r,2r)-1-hydroxy-1,2-dihydronaphthalen-2-yl] acetate Chemical compound C1=CC=C2[C@@H](O)[C@H](OC(=O)C)C=CC2=C1 RYDUJHSMAWBEJS-VXGBXAGGSA-N 0.000 claims 1
- ROPBGIJMSJNDNA-VQTJNVASSA-N [(1r,2s)-1-[(4-methylphenyl)sulfonylamino]-1,2-dihydronaphthalen-2-yl] 2,2-dimethylpropanoate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N[C@@H]1C2=CC=CC=C2C=C[C@@H]1OC(=O)C(C)(C)C ROPBGIJMSJNDNA-VQTJNVASSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- 229960004217 benzyl alcohol Drugs 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- HQQVPORFYMXMQJ-FCHUYYIVSA-N n,4-dimethyl-n-[(1r,2s)-2-pyrrolidin-1-yl-1,2-dihydronaphthalen-1-yl]benzenesulfonamide Chemical compound N1([C@@H]2[C@@H](C3=CC=CC=C3C=C2)N(C)S(=O)(=O)C=2C=CC(C)=CC=2)CCCC1 HQQVPORFYMXMQJ-FCHUYYIVSA-N 0.000 claims 1
- BRZJQWUGBCALQM-IZZNHLLZSA-N n-[(1r,2s)-2-(3,4-dihydro-1h-isoquinolin-2-yl)-1,2-dihydronaphthalen-1-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N[C@@H]1C2=CC=CC=C2C=C[C@@H]1N1CC2=CC=CC=C2CC1 BRZJQWUGBCALQM-IZZNHLLZSA-N 0.000 claims 1
- SEODCRTWVPVWAX-IZZNHLLZSA-N n-[(1r,2s)-2-(3,4-dihydro-2h-quinolin-1-yl)-1,2-dihydronaphthalen-1-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N[C@@H]1C2=CC=CC=C2C=C[C@@H]1N1C2=CC=CC=C2CCC1 SEODCRTWVPVWAX-IZZNHLLZSA-N 0.000 claims 1
- LXGFJWYJNAXJTQ-ZWKOTPCHSA-N n-[(1r,2s)-2-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl]-4-methylbenzenesulfonamide Chemical compound N([C@@H]1C2=CC=CC=C2CC[C@@H]1OC)S(=O)(=O)C1=CC=C(C)C=C1 LXGFJWYJNAXJTQ-ZWKOTPCHSA-N 0.000 claims 1
- RCWXXLMNTGEPOR-HOTGVXAUSA-N n-[(1s,2s)-1-hydroxy-1,2-dihydronaphthalen-2-yl]benzenesulfonamide Chemical compound N([C@@H]1[C@H](C2=CC=CC=C2C=C1)O)S(=O)(=O)C1=CC=CC=C1 RCWXXLMNTGEPOR-HOTGVXAUSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
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- C07C215/44—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton bound to carbon atoms of the same ring or condensed ring system
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- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
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- C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C07C43/196—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal groups
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- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
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- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
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- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Molecular Biology (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
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- Other In-Based Heterocyclic Compounds (AREA)
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Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9903930A SE9903930D0 (sv) | 1999-10-29 | 1999-10-29 | Novel compounds and a novel process for their preparation |
Publications (1)
Publication Number | Publication Date |
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ZA200203050B true ZA200203050B (en) | 2003-07-17 |
Family
ID=20417551
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200203050A ZA200203050B (en) | 1999-10-29 | 2002-04-17 | Novel hydronaphtalene compounds, prepared by a rhodium catalyzed ring opening reaction in the presence of phosphine ligand. |
Country Status (20)
Country | Link |
---|---|
US (4) | US6525068B1 (xx) |
EP (2) | EP1228024B1 (xx) |
JP (1) | JP2003512446A (xx) |
KR (1) | KR100741177B1 (xx) |
CN (1) | CN1231439C (xx) |
AT (1) | ATE275120T1 (xx) |
AU (1) | AU776118B2 (xx) |
BR (1) | BR0015117A (xx) |
CA (1) | CA2387675C (xx) |
DE (1) | DE60013471T2 (xx) |
ES (1) | ES2225253T3 (xx) |
HK (1) | HK1047083B (xx) |
IL (2) | IL149368A0 (xx) |
MX (1) | MXPA02004224A (xx) |
NO (1) | NO328015B1 (xx) |
NZ (1) | NZ518451A (xx) |
PT (1) | PT1228024E (xx) |
SE (1) | SE9903930D0 (xx) |
WO (1) | WO2001030734A1 (xx) |
ZA (1) | ZA200203050B (xx) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE602004021358D1 (de) * | 2003-03-25 | 2009-07-16 | Fournier Lab Sa | Benzosulfonamide derivate, deren verfahren zum herstellung, und deren verwendung zur behandlung von schmerzen |
FR2852958B1 (fr) * | 2003-03-25 | 2005-06-24 | Fournier Lab Sa | Nouveaux derives de benzenesulfonamides et leur utilisation en therapeutique |
US7638515B2 (en) | 2003-10-08 | 2009-12-29 | Bayer Schering Pharma Aktiengesellschaft | Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
JP4638438B2 (ja) | 2003-10-08 | 2011-02-23 | バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト | テトラヒドロナフタレン誘導体類、それらの生成方法及び抗−炎症剤としてのそれらの使用 |
US7662821B2 (en) | 2003-10-08 | 2010-02-16 | Bayer Schering Pharma Ag | Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
US20080153859A1 (en) | 2004-04-05 | 2008-06-26 | Hartmut Rehwinkel | Multiply-substituted tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
DE102005017316A1 (de) * | 2005-04-14 | 2006-10-19 | Schering Ag | Tetrahydronaphthalinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
EP1834948A1 (de) | 2006-03-15 | 2007-09-19 | Bayer Schering Pharma Aktiengesellschaft | Tetrahydronaphthalinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
EP2070903A1 (en) | 2007-12-12 | 2009-06-17 | Laboratorios del Dr. Esteve S.A. | Microwave-assisted ring opening reaction |
EP2070904A1 (en) | 2007-12-12 | 2009-06-17 | Laboratorios Del. Dr. Esteve, S.A. | Rhodium-phosphorus complexes and their use in ring opening reactions |
KR101229822B1 (ko) | 2008-03-04 | 2013-02-05 | 연세대학교 산학협력단 | 혈관신생 억제용 약제학적 조성물 |
EP2098511A1 (en) * | 2008-03-07 | 2009-09-09 | Solvias AG | Process for preparing compounds containing a hydronaphtalene structure with an unsymmetrically substituted benzene ring |
JP5656364B2 (ja) * | 2009-04-20 | 2015-01-21 | 株式会社トクヤマ | ナフトピラン誘導体の製造方法 |
CN104744321A (zh) * | 2010-01-27 | 2015-07-01 | 武田药品工业株式会社 | 用于抑制由抗癌剂诱导的外周神经障碍的化合物 |
JP6236785B2 (ja) * | 2012-02-28 | 2017-11-29 | 株式会社リコー | アリールアミン化合物、有機el用材料およびその製造方法 |
CN105399752B (zh) * | 2015-11-04 | 2019-03-15 | 云南民族大学 | 一种新型化合物及其制备方法和应用 |
US11560384B2 (en) | 2017-05-04 | 2023-01-24 | University Of Utah Research Foundation | Benzonorbornadiene derivatives and reactions thereof |
CN108863855B (zh) * | 2018-05-29 | 2020-12-15 | 云南民族大学 | 一种合成(1r,2s)-1,2-二氢化萘-1,2-二胺衍生物的方法 |
CN111471005B (zh) * | 2020-05-21 | 2023-04-07 | 南方科技大学 | 一种吲哚-二氢化萘类化合物及其制备方法和应用 |
CN116459873A (zh) * | 2022-01-12 | 2023-07-21 | 万华化学集团股份有限公司 | 一种烯属不饱和化合物羰基化催化剂及其制备方法、应用 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
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AU4031097A (en) * | 1997-08-27 | 1999-03-16 | Kyowa Hakko Kogyo Co. Ltd. | Process for preparing optically active 1,2-diols |
-
1999
- 1999-10-29 SE SE9903930A patent/SE9903930D0/xx unknown
-
2000
- 2000-10-26 BR BR0015117-3A patent/BR0015117A/pt not_active Application Discontinuation
- 2000-10-26 NZ NZ518451A patent/NZ518451A/en unknown
- 2000-10-26 CA CA002387675A patent/CA2387675C/en not_active Expired - Fee Related
- 2000-10-26 EP EP00975109A patent/EP1228024B1/en not_active Expired - Lifetime
- 2000-10-26 US US09/763,759 patent/US6525068B1/en not_active Expired - Fee Related
- 2000-10-26 WO PCT/SE2000/002090 patent/WO2001030734A1/en active IP Right Grant
- 2000-10-26 KR KR1020027005436A patent/KR100741177B1/ko not_active IP Right Cessation
- 2000-10-26 DE DE60013471T patent/DE60013471T2/de not_active Expired - Lifetime
- 2000-10-26 PT PT00975109T patent/PT1228024E/pt unknown
- 2000-10-26 ES ES00975109T patent/ES2225253T3/es not_active Expired - Lifetime
- 2000-10-26 EP EP04015462A patent/EP1498406A1/en not_active Withdrawn
- 2000-10-26 IL IL14936800A patent/IL149368A0/xx unknown
- 2000-10-26 MX MXPA02004224A patent/MXPA02004224A/es active IP Right Grant
- 2000-10-26 AU AU13206/01A patent/AU776118B2/en not_active Ceased
- 2000-10-26 CN CNB008177481A patent/CN1231439C/zh not_active Expired - Fee Related
- 2000-10-26 AT AT00975109T patent/ATE275120T1/de not_active IP Right Cessation
- 2000-10-26 JP JP2001533091A patent/JP2003512446A/ja active Pending
-
2002
- 2002-04-17 ZA ZA200203050A patent/ZA200203050B/en unknown
- 2002-04-25 NO NO20021968A patent/NO328015B1/no not_active IP Right Cessation
- 2002-04-25 IL IL149368A patent/IL149368A/en not_active IP Right Cessation
- 2002-11-28 HK HK02108588.9A patent/HK1047083B/zh not_active IP Right Cessation
- 2002-12-12 US US10/317,183 patent/US6784210B2/en not_active Expired - Fee Related
-
2004
- 2004-05-28 US US10/855,783 patent/US7420003B2/en not_active Expired - Fee Related
-
2008
- 2008-07-28 US US12/219,752 patent/US20080300271A1/en not_active Abandoned
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