NO128604B - - Google Patents

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Info

Publication number: NO128604B
Authority: NO; Norway
Prior art keywords: methoxy; naphthyl; formula; compound; ether
Prior art date: 1969-09-30

Application number

NO514569A

Other languages

English (en)

Norwegian (no)

Inventor

J Fried

I Harrison

P Nelson

Original Assignee

Syntex Corp

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.)

1969-09-30

Filing date

1969-12-29

Publication date

1973-12-17

1969-12-29 Application filed by Syntex Corp filed Critical Syntex Corp

1973-12-17 Publication of NO128604B publication Critical patent/NO128604B/no

Links

RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 84
150000001875 compounds Chemical class 0.000 claims description 29
238000000034 method Methods 0.000 claims description 28
239000011541 reaction mixture Substances 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 23
LTRANDSQVZFZDG-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)propan-1-ol Chemical compound C1=C(C(C)CO)C=CC2=CC(OC)=CC=C21 LTRANDSQVZFZDG-UHFFFAOYSA-N 0.000 claims description 16
-1 2-(6-methoxy-2-naphthyl)-1-propyl Chemical group 0.000 claims description 13
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 13
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
229910052700 potassium Inorganic materials 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 7
229910052744 lithium Inorganic materials 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
MJWURUPGNUFKMR-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)prop-2-enoic acid Chemical compound C1=C(C(=C)C(O)=O)C=CC2=CC(OC)=CC=C21 MJWURUPGNUFKMR-UHFFFAOYSA-N 0.000 claims description 5
238000005984 hydrogenation reaction Methods 0.000 claims description 5
229910052987 metal hydride Inorganic materials 0.000 claims description 5
150000004681 metal hydrides Chemical class 0.000 claims description 5
UPEGIZOAIZVQDQ-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)-2-methyloxirane Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C1(C)CO1 UPEGIZOAIZVQDQ-UHFFFAOYSA-N 0.000 claims description 4
VDWXOLWUMXBPHB-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)prop-2-en-1-ol Chemical compound C1=C(C(=C)CO)C=CC2=CC(OC)=CC=C21 VDWXOLWUMXBPHB-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
239000002841 Lewis acid Substances 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 3
150000007517 lewis acids Chemical class 0.000 claims description 3
230000001225 therapeutic effect Effects 0.000 claims description 3
DVQOTDYKJNEHNJ-UHFFFAOYSA-N 2-methoxy-6-prop-2-enylnaphthalene Chemical compound C1=C(CC=C)C=CC2=CC(OC)=CC=C21 DVQOTDYKJNEHNJ-UHFFFAOYSA-N 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
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 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 8
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 8
239000012071 phase Substances 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
239000011591 potassium Substances 0.000 description 6
238000007796 conventional method Methods 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000005406 washing Methods 0.000 description 4
GGWCZBGAIGGTDA-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)ethanone Chemical compound C1=C(C(C)=O)C=CC2=CC(OC)=CC=C21 GGWCZBGAIGGTDA-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
229930040373 Paraformaldehyde Natural products 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
MBRGPNPWNNBULN-UHFFFAOYSA-M [Br-].COC=1C=C2C=CC(=CC2=CC1)C(C)[Mg+] Chemical compound [Br-].COC=1C=C2C=CC(=CC2=CC1)C(C)[Mg+] MBRGPNPWNNBULN-UHFFFAOYSA-M 0.000 description 3
KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
229920002866 paraformaldehyde Polymers 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
CEERUWZBFFNSRP-UHFFFAOYSA-N COC=1C=C2C=CC(=CC2=CC1)C(C)[Cd] Chemical compound COC=1C=C2C=CC(=CC2=CC1)C(C)[Cd] CEERUWZBFFNSRP-UHFFFAOYSA-N 0.000 description 2
RQCKEFHDNCHKCZ-UHFFFAOYSA-N COC=1C=C2C=CC(=CC2=CC1)C(C)[Na] Chemical compound COC=1C=C2C=CC(=CC2=CC1)C(C)[Na] RQCKEFHDNCHKCZ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
206010061218 Inflammation Diseases 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
239000012448 Lithium borohydride Substances 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
150000001639 boron compounds Chemical class 0.000 description 2
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 2
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
XEEITBAXIABDJT-UHFFFAOYSA-N 2-(1-bromoethyl)-6-methoxynaphthalene Chemical compound C1=C(C(C)Br)C=CC2=CC(OC)=CC=C21 XEEITBAXIABDJT-UHFFFAOYSA-N 0.000 description 1
CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
208000010392 Bone Fractures Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
BGLUHKXZAFGLNM-UHFFFAOYSA-N COC=1C=C2C=CC(=CC2=CC1)C(C)[K] Chemical compound COC=1C=C2C=CC(=CC2=CC1)C(C)[K] BGLUHKXZAFGLNM-UHFFFAOYSA-N 0.000 description 1
ZALIYRZMVXSJPM-UHFFFAOYSA-N COC=1C=C2C=CC(=CC2=CC1)C(C)[Li] Chemical compound COC=1C=C2C=CC(=CC2=CC1)C(C)[Li] ZALIYRZMVXSJPM-UHFFFAOYSA-N 0.000 description 1
QFCVSLOOCXNECI-UHFFFAOYSA-N COC=1C=C2C=CC(=CC2=CC1)C(C)[Zn] Chemical compound COC=1C=C2C=CC(=CC2=CC1)C(C)[Zn] QFCVSLOOCXNECI-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
206010010254 Concussion Diseases 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
208000006670 Multiple fractures Diseases 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
ZLNQCMDQGHYICR-UHFFFAOYSA-M [Cl-].COC=1C=C2C=CC(=CC2=CC1)C(C)[Mg+] Chemical compound [Cl-].COC=1C=C2C=CC(=CC2=CC1)C(C)[Mg+] ZLNQCMDQGHYICR-UHFFFAOYSA-M 0.000 description 1
HQFSKHGKXPADLC-UHFFFAOYSA-M [I-].COC=1C=C2C=CC(=CC2=CC1)C(C)[Mg+] Chemical compound [I-].COC=1C=C2C=CC(=CC2=CC1)C(C)[Mg+] HQFSKHGKXPADLC-UHFFFAOYSA-M 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
230000009514 concussion Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Inorganic materials [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 1
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Inorganic materials [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000002346 musculoskeletal system Anatomy 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
210000001519 tissue Anatomy 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
230000007306 turnover Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds

Landscapes

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

NO514569A 1969-09-30 1969-12-29 NO128604B (da)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date
US86249869A	1969-09-30	1969-09-30
US86245469A	1969-09-30	1969-09-30
US86245369A	1969-09-30	1969-09-30
US86247569A	1969-09-30	1969-09-30
US86245569A	1969-09-30	1969-09-30
US86250169A	1969-09-30	1969-09-30
US86247169A	1969-09-30	1969-09-30

Publications (1)

Publication Number	Publication Date
NO128604B true NO128604B (da)	1973-12-17

Family

ID=27569931

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO514569A NO128604B (da)	1969-09-30	1969-12-29

Country Status (7)

Country	Link
JP (1)	JPS516667B1 (da)
BR (1)	BR6915472D0 (da)
CH (6)	CH547248A (da)
DK (1)	DK145338C (da)
FI (1)	FI50620C (da)
FR (1)	FR2068539A1 (da)
NO (1)	NO128604B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS54128261U (da) *	1978-02-28	1979-09-06
JP2023112428A (ja) *	2022-02-01	2023-08-14	株式会社東芝	磁気ヘッド及び磁気記録再生装置

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3641161A (en) *	1968-07-02	1972-02-08	Syntex Corp	Naphthyl alkanols

1969
- 1969-12-19 BR BR21547269A patent/BR6915472D0/pt unknown
- 1969-12-29 NO NO514569A patent/NO128604B/no unknown
- 1969-12-30 DK DK691669A patent/DK145338C/da not_active IP Right Cessation
1970
- 1970-02-25 FI FI50770A patent/FI50620C/fi active
- 1970-03-18 FR FR7009733A patent/FR2068539A1/fr active Granted
- 1970-03-24 JP JP2479870A patent/JPS516667B1/ja active Pending
- 1970-08-21 CH CH547248D patent/CH547248A/xx not_active IP Right Cessation
- 1970-08-21 CH CH547246D patent/CH547246A/xx not_active IP Right Cessation
- 1970-08-21 CH CH1442473A patent/CH549545A/xx not_active IP Right Cessation
- 1970-08-21 CH CH1442373A patent/CH549544A/xx not_active IP Right Cessation
- 1970-08-21 CH CH547247D patent/CH547247A/xx not_active IP Right Cessation
- 1970-08-21 CH CH1256970A patent/CH543467A/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK145338C (da)	1983-03-21
FI50620B (da)	1976-02-02
FI50620C (fi)	1976-05-10
CH547248A (de)	1974-03-29
FR2068539A1 (en)	1971-08-27
FR2068539B1 (da)	1974-02-22
CH549544A (de)	1974-05-31
CH547246A (de)	1974-03-29
CH547247A (de)	1974-03-29
BR6915472D0 (pt)	1973-06-14
CH549545A (de)	1974-05-31
DK145338B (da)	1982-11-01
JPS516667B1 (da)	1976-03-01
CH543467A (de)	1973-10-31

Publication	Publication Date	Title
Partridge et al.	1974	Vitamin D3 Metabolites I. Synthesis of 25‐hydroxycholesterol
NO742888L (da)	1975-03-17
EP0183169B1 (de)	1989-05-10	Halogen-hydroxy-flavone
Letsinger et al.	1965	Intramolecular Catalysis in Addition of Carboxyl to Carbon-Carbon Triple Bonds1
NO128604B (da)	1973-12-17
US3651148A (en)	1972-03-21	2-(6-methoxy-2-naphthyl)-1-propyl boranes
Anet et al.	1956	STUDIES IN THE WAGNER-MEERWEIN REARRANGEMENT. PART I
US2175843A (en)	1939-10-10	Polyene carboxylic acids and esters and manufacture thereof
NO750819L (da)	1975-09-23
Clark	1931	Deguelin. I. The preparation, purification and properties of deguelin, a constituent of certain tropical fish-poisoning plants
US2648667A (en)	1953-08-11	Esters of 1-azabicycloalkanols
Kauer et al.	1968	Tetramers of acetylenedicarboxylic esters
Cornejo et al.	1983	Benzo [e] isobenzofuran. Formation and reactions of the parent and alkoxy-substituted derivatives
CN113527075B (zh)	2022-10-21	一种一步法合成5-氯-1-茚酮的制备方法
NO823439L (no)	1983-04-18	Fremgangsmaate for fremstilling av 5-fenyl-25-pentanol
Kato et al.	1987	Total synthesis of dl-siccanin and dl-siccanochromene E
IL29340A (en)	1972-02-29	Dibenzoazepine derivatives and their preparation
Southwick et al.	1955	The addition of N-bromomorpholine to benzalacetophenone
Jacobson	1962	Insect sex attractants. III. The optical resolution of DL-10-acetoxy-cis-7-hexadecen-1-ol
US3499037A (en)	1970-03-03	Preparation of trifluoromethyl substituted dibenzocycloheptenes
US3038002A (en)	1962-06-05	Syntheses of alpha-methoxyphenylacetates
DK165785B (da)	1993-01-18	Fremgangsmaade til fremstilling af trifenylbutenderivater og farmaceutisk acceptable syreadditionssalte deraf og mellemprodukter til brug ved fremgangsmaaden
Ball et al.	1959	5, 6-DIDEOXY-l-ARABINO-HEXOSE (5-DEOXY-5-C-METHYL-l-ARABINOSE)
DE2039639C2 (de)	1982-08-05	Verfahren zur Herstellung von l-2-(6-Methoxy-2-naphthyl)-1-propanol
Bu'Lock et al.	1957	216. Chemistry of the higher fungi. Part VII. Odyssic acid and odyssin