CA1088537A - Phenylpiperazinotetrahydronaphtols et leurs derives - Google Patents

Phenylpiperazinotetrahydronaphtols et leurs derives

Info

Publication number: CA1088537A
Authority: CA; Canada
Prior art keywords: compound; tetrahydro; piperazinyl; methoxyphenyl; naphthalenol
Prior art date: 1976-09-02
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

CA260,395A

Other languages

English (en)

Inventor

Michael E. Condon

Frederic P. Hauck

Joyce A. Reid

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.)

ER Squibb and Sons LLC

Original Assignee

ER Squibb and Sons LLC

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.)

1976-09-02

Filing date

1976-09-02

Publication date

1980-10-28

1976-09-02 Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC

1976-09-02 Priority to CA260,395A priority Critical patent/CA1088537A/fr

1980-10-28 Application granted granted Critical

1980-10-28 Publication of CA1088537A publication Critical patent/CA1088537A/fr

Status Expired legal-status Critical Current

Links

NHXHOSXLYPSXQR-UHFFFAOYSA-N 2-phenyl-1-piperazin-1-yl-3,4-dihydro-2h-naphthalen-1-ol Chemical class C1CC2=CC=CC=C2C(O)(N2CCNCC2)C1C1=CC=CC=C1 NHXHOSXLYPSXQR-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 129
125000000217 alkyl group Chemical group 0.000 claims abstract description 28
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
239000001257 hydrogen Substances 0.000 claims abstract description 26
-1 alkoxy alkyl-thio Chemical group 0.000 claims abstract description 25
125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
229910052736 halogen Inorganic materials 0.000 claims abstract description 15
150000002367 halogens Chemical group 0.000 claims abstract description 15
125000003118 aryl group Chemical group 0.000 claims abstract description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
239000002253 acid Substances 0.000 claims abstract description 8
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 16
238000000034 method Methods 0.000 claims description 88
229950011260 betanaphthol Drugs 0.000 claims description 21
150000002148 esters Chemical class 0.000 claims description 12
FCUCVLJUJUYGIO-WOJBJXKFSA-N (2r,3r)-5,8-dimethoxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1CN([C@@H]2CC=3C(OC)=CC=C(C=3C[C@H]2O)OC)CCN1C1=CC=CC=C1OC FCUCVLJUJUYGIO-WOJBJXKFSA-N 0.000 claims description 10
KJIUCCZHJOBTNQ-UYAOXDASSA-N (6r,7r)-6-[4-(2-methoxyphenyl)piperazin-1-yl]-5,6,7,8-tetrahydronaphthalene-1,7-diol Chemical compound COC1=CC=CC=C1N1CCN([C@H]2[C@@H](CC3=C(O)C=CC=C3C2)O)CC1 KJIUCCZHJOBTNQ-UYAOXDASSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
YPVCEDVXIGMBIR-UYAOXDASSA-N (6r,7r)-7-[4-(2-methoxyphenyl)piperazin-1-yl]-5,6,7,8-tetrahydronaphthalene-1,6-diol Chemical compound COC1=CC=CC=C1N1CCN([C@H]2[C@@H](CC3=CC=CC(O)=C3C2)O)CC1 YPVCEDVXIGMBIR-UYAOXDASSA-N 0.000 claims description 4
RGKOZRJYVZRBKE-WOJBJXKFSA-N (2r,3r)-5,8-dimethoxy-3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1CN([C@@H]2CC=3C(OC)=CC=C(C=3C[C@H]2O)OC)CCN1C1=CC=CC(C(F)(F)F)=C1 RGKOZRJYVZRBKE-WOJBJXKFSA-N 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 3
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
230000008569 process Effects 0.000 claims 82
XZWLPZZTDUEMJT-WOJBJXKFSA-N (2r,3r)-3-(4-phenylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1CN([C@@H]2CC3=CC=CC=C3C[C@H]2O)CCN1C1=CC=CC=C1 XZWLPZZTDUEMJT-WOJBJXKFSA-N 0.000 claims 4
LQOAZKVJTFFSOZ-YLJYHZDGSA-N (6r,7r)-7-[4-(2-methoxyphenyl)piperazin-1-yl]-5,6,7,8-tetrahydronaphthalene-1,4,6-triol Chemical compound COC1=CC=CC=C1N1CCN([C@H]2[C@@H](CC3=C(O)C=CC(O)=C3C2)O)CC1 LQOAZKVJTFFSOZ-YLJYHZDGSA-N 0.000 claims 3
VRHUUOVABFUVRE-WOJBJXKFSA-N (2r,3r)-3-[4-(2-chlorophenyl)piperazin-1-yl]-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1CN([C@@H]2CC=3C(OC)=CC=C(C=3C[C@H]2O)OC)CCN1C1=CC=CC=C1Cl VRHUUOVABFUVRE-WOJBJXKFSA-N 0.000 claims 2
AZJADVQIPNYBNW-NHCUHLMSSA-N (2r,3r)-3-[4-(2-ethylsulfanylphenyl)piperazin-1-yl]-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound CCSC1=CC=CC=C1N1CCN([C@H]2[C@@H](CC3=C(OC)C=CC(OC)=C3C2)O)CC1 AZJADVQIPNYBNW-NHCUHLMSSA-N 0.000 claims 2
IPPXJZLZPHJGMU-NHCUHLMSSA-N (2r,3r)-5,8-dimethoxy-3-[4-(2-methylphenyl)piperazin-1-yl]-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1CN([C@@H]2CC=3C(OC)=CC=C(C=3C[C@H]2O)OC)CCN1C1=CC=CC=C1C IPPXJZLZPHJGMU-NHCUHLMSSA-N 0.000 claims 2
BPAOOCZHEUXGQF-WOJBJXKFSA-N (2r,3r)-5-methoxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1CN([C@H]2[C@H](O)CC=3C=CC=C(C=3C2)OC)CCN1C1=CC=CC=C1OC BPAOOCZHEUXGQF-WOJBJXKFSA-N 0.000 claims 2
CCSBAKJTHQLUDG-WOJBJXKFSA-N (2r,3r)-6,7-dimethoxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound COC1=CC=CC=C1N1CCN([C@H]2[C@@H](CC3=CC(OC)=C(OC)C=C3C2)O)CC1 CCSBAKJTHQLUDG-WOJBJXKFSA-N 0.000 claims 2
ZWOZHHCKUCCDCG-NHCUHLMSSA-N (2r,3r)-6-methoxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1CN([C@H]2[C@H](O)CC3=CC=C(C=C3C2)OC)CCN1C1=CC=CC=C1OC ZWOZHHCKUCCDCG-NHCUHLMSSA-N 0.000 claims 2
XRNGKPAMZZYPDU-NHCUHLMSSA-N (2r,3r)-7-methoxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1CN([C@@H]2CC3=CC=C(C=C3C[C@H]2O)OC)CCN1C1=CC=CC=C1OC XRNGKPAMZZYPDU-NHCUHLMSSA-N 0.000 claims 2
KTVKISDWOUTDFN-WOJBJXKFSA-N (2r,3r)-8-methoxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1CN([C@@H]2CC=3C=CC=C(C=3C[C@H]2O)OC)CCN1C1=CC=CC=C1OC KTVKISDWOUTDFN-WOJBJXKFSA-N 0.000 claims 2
SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
KHIGSKORPRRTRN-WOJBJXKFSA-N (2r,3r)-3-[4-(2-methoxyphenyl)piperazin-1-yl]-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound COC1=CC=CC=C1N1CCN([C@H]2[C@@H](CC3=CC=CC=C3C2)O)CC1 KHIGSKORPRRTRN-WOJBJXKFSA-N 0.000 claims 1
DNMQWWNIMKNOGN-WOJBJXKFSA-N (2r,3r)-3-[4-(2-methoxyphenyl)piperazin-1-yl]-1,2,3,4-tetrahydronaphthalene-2,6-diol Chemical compound COC1=CC=CC=C1N1CCN([C@H]2[C@@H](CC3=CC=C(O)C=C3C2)O)CC1 DNMQWWNIMKNOGN-WOJBJXKFSA-N 0.000 claims 1
UNNBICHWRLYXIW-WOJBJXKFSA-N (2r,3r)-3-[4-(2-methoxyphenyl)piperazin-1-yl]-1,2,3,4-tetrahydronaphthalene-2,7-diol Chemical compound COC1=CC=CC=C1N1CCN([C@H]2[C@@H](CC3=CC(O)=CC=C3C2)O)CC1 UNNBICHWRLYXIW-WOJBJXKFSA-N 0.000 claims 1
HMFWSOIWJXKFQA-WOJBJXKFSA-N (2r,3r)-5,6,8-trimethoxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1CN([C@@H]2CC=3C(OC)=C(OC)C=C(C=3C[C@H]2O)OC)CCN1C1=CC=CC=C1OC HMFWSOIWJXKFQA-WOJBJXKFSA-N 0.000 claims 1
UDNNSIKYNPWOCX-WOJBJXKFSA-N (2r,3r)-5,7,8-trimethoxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1CN([C@H]2[C@H](O)CC=3C(OC)=C(OC)C=C(C=3C2)OC)CCN1C1=CC=CC=C1OC UDNNSIKYNPWOCX-WOJBJXKFSA-N 0.000 claims 1
239000002220 antihypertensive agent Substances 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 94
239000000243 solution Substances 0.000 description 55
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
235000013350 formula milk Nutrition 0.000 description 39
239000000203 mixture Substances 0.000 description 37
238000002844 melting Methods 0.000 description 32
230000008018 melting Effects 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 25
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000000463 material Substances 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
238000001953 recrystallisation Methods 0.000 description 15
239000008096 xylene Substances 0.000 description 15
239000007787 solid Substances 0.000 description 14
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
239000002178 crystalline material Substances 0.000 description 11
238000001035 drying Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
XZIDAWSWGWZKOO-UHFFFAOYSA-N 3,6-dimethoxy-1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene Chemical compound C1C2OC2CC2=C1C(OC)=CC=C2OC XZIDAWSWGWZKOO-UHFFFAOYSA-N 0.000 description 8
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
239000006260 foam Substances 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
238000001665 trituration Methods 0.000 description 8
KXSWSFNGQCBWQA-UHFFFAOYSA-N 1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene Chemical class C1C2=CC=CC=C2CC2C1O2 KXSWSFNGQCBWQA-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
238000001816 cooling Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
239000012043 crude product Substances 0.000 description 6
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
239000003610 charcoal Substances 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
238000004042 decolorization Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
FUPIVZHYVSCYLX-UHFFFAOYSA-N 1,4-dihydronaphthalene Chemical class C1=CC=C2CC=CCC2=C1 FUPIVZHYVSCYLX-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
239000013058 crude material Substances 0.000 description 3
238000010828 elution Methods 0.000 description 3
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
GRSSLJQGWWIXEA-NXEZZACHSA-N (2r,3r)-3-amino-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1[C@@H](O)[C@H](N)CC2=C1C(OC)=CC=C2OC GRSSLJQGWWIXEA-NXEZZACHSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
NJQCJWIWPUOWGU-UHFFFAOYSA-N 5,8-dimethoxynaphthalen-2-ol Chemical compound OC1=CC=C2C(OC)=CC=C(OC)C2=C1 NJQCJWIWPUOWGU-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
150000002085 enols Chemical class 0.000 description 2
HBFXVTVOSLPOEY-UHFFFAOYSA-N ethoxyethane;2-propan-2-yloxypropane Chemical compound CCOCC.CC(C)OC(C)C HBFXVTVOSLPOEY-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
229960000443 hydrochloric acid Drugs 0.000 description 2
235000011167 hydrochloric acid Nutrition 0.000 description 2
150000002440 hydroxy compounds Chemical class 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
239000003495 polar organic solvent Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
239000000523 sample Substances 0.000 description 2
239000012056 semi-solid material Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000011345 viscous material Substances 0.000 description 2
ONSBNJDWQUGGAG-UHFFFAOYSA-N (3-acetyloxy-1a,2,7,7a-tetrahydronaphtho[6,7-b]oxiren-6-yl) acetate Chemical compound C1C2OC2CC2=C1C(OC(C)=O)=CC=C2OC(=O)C ONSBNJDWQUGGAG-UHFFFAOYSA-N 0.000 description 1
WICKLEOONJPMEQ-UHFFFAOYSA-N 1-(2-methylphenyl)piperazine Chemical compound CC1=CC=CC=C1N1CCNCC1 WICKLEOONJPMEQ-UHFFFAOYSA-N 0.000 description 1
PBXHQVCPIWPYOZ-UHFFFAOYSA-N 1a,2,7,7a-tetrahydronaphtho[6,7-b]oxiren-3-ol Chemical compound C1C2OC2CC2=C1C=CC=C2O PBXHQVCPIWPYOZ-UHFFFAOYSA-N 0.000 description 1
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical group CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
JQQKTEXFNXKDIQ-UHFFFAOYSA-N 2-chloro-1-phenylpiperazine Chemical compound ClC1CNCCN1C1=CC=CC=C1 JQQKTEXFNXKDIQ-UHFFFAOYSA-N 0.000 description 1
PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
CYTQZSWTAYTKHZ-UHFFFAOYSA-N 3,4,6-trimethoxy-1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene Chemical compound C1C2OC2CC2=C1C(OC)=C(OC)C=C2OC CYTQZSWTAYTKHZ-UHFFFAOYSA-N 0.000 description 1
GEHQAAXFFSBTCG-UHFFFAOYSA-N 3,6-dichloro-1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene Chemical group C1C2OC2CC2=C1C(Cl)=CC=C2Cl GEHQAAXFFSBTCG-UHFFFAOYSA-N 0.000 description 1
DZRSOVOHSHIILP-UHFFFAOYSA-N 3,6-dimethyl-1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene Chemical group C1C2OC2CC2=C1C(C)=CC=C2C DZRSOVOHSHIILP-UHFFFAOYSA-N 0.000 description 1
NXDYPXZLPCZHSR-UHFFFAOYSA-N 4,5-dimethoxy-1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene Chemical compound C1C2OC2CC2=C1C=C(OC)C(OC)=C2 NXDYPXZLPCZHSR-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
239000004215 Carbon black (E152) Substances 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
241000490229 Eucephalus Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
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 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
ASGJEMPQQVNTGO-UHFFFAOYSA-N benzene chloroform Chemical compound C(Cl)(Cl)Cl.C1=CC=CC=C1.C1=CC=CC=C1 ASGJEMPQQVNTGO-UHFFFAOYSA-N 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229940112822 chewing gum Drugs 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
201000006747 infectious mononucleosis Diseases 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PSKXFOWSYBJDIR-HZPDHXFCSA-N n-[(2r,3r)-3-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]benzamide Chemical compound N([C@@H]1CC=2C(OC)=CC=C(C=2C[C@H]1O)OC)C(=O)C1=CC=CC=C1 PSKXFOWSYBJDIR-HZPDHXFCSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical group O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1

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CA260,395A 1976-09-02 1976-09-02 Phenylpiperazinotetrahydronaphtols et leurs derives Expired CA1088537A (fr)

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CA260,395A CA1088537A (fr)	1976-09-02	1976-09-02	Phenylpiperazinotetrahydronaphtols et leurs derives

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Application Number	Priority Date	Filing Date	Title
CA260,395A CA1088537A (fr)	1976-09-02	1976-09-02	Phenylpiperazinotetrahydronaphtols et leurs derives

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CA1088537A true CA1088537A (fr)	1980-10-28

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CA260,395A Expired CA1088537A (fr)	1976-09-02	1976-09-02	Phenylpiperazinotetrahydronaphtols et leurs derives

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5151446A (en) *	1989-09-25	1992-09-29	Northwestern University	Substituted 2-amidotetralins as melatonin agonists and antagonists

1976
- 1976-09-02 CA CA260,395A patent/CA1088537A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5151446A (en) *	1989-09-25	1992-09-29	Northwestern University	Substituted 2-amidotetralins as melatonin agonists and antagonists

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1997-10-28	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 19971028

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CA1088537A - Phenylpiperazinotetrahydronaphtols et leurs derives - Google Patents

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ID=4106768

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