NO753418L - - Google Patents

Info

Publication number: NO753418L
Authority: NO; Norway
Prior art keywords: dibenzo; acid; formula; ethylenedioxy; ester
Prior art date: 1975-09-08

Application number

NO753418A

Other languages

English (en)

Norwegian (no)

Inventor

P H Nelson

K G Untch

J P Dunn

Original Assignee

Syntex Inc

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.)

1975-09-08

Filing date

1975-10-09

Publication date

1977-03-09

1975-10-09 Application filed by Syntex Inc filed Critical Syntex Inc

1977-03-09 Publication of NO753418L publication Critical patent/NO753418L/no

Links

QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 41
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 40
239000002253 acid Substances 0.000 claims description 24
150000002148 esters Chemical class 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 22
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
238000000034 method Methods 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
-1 cyano, carboxy Chemical group 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229940080818 propionamide Drugs 0.000 claims description 6
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
125000004185 ester group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 5
XOUXVMOQGKREIE-UHFFFAOYSA-N 2-(11-oxodibenzo[1,2-a:2',1'-d][7]annulen-3-yl)propanenitrile Chemical group C1=CC2=CC=CC=C2C(=O)C2=CC=C(C(C#N)C)C=C21 XOUXVMOQGKREIE-UHFFFAOYSA-N 0.000 claims 1
ACVOZKLYYNYZPN-UHFFFAOYSA-N 2-spiro[1,3-dioxolane-2,11'-dibenzo[1,2-a:1',2'-e][7]annulene]-3'-ylacetamide Chemical group C=1C(CC(=O)N)=CC=C2C=1C=CC1=CC=CC=C1C21OCCO1 ACVOZKLYYNYZPN-UHFFFAOYSA-N 0.000 claims 1
KTAVNNANNXIHFO-UHFFFAOYSA-N 2-spiro[1,3-dioxolane-2,11'-dibenzo[1,2-a:1',2'-e][7]annulene]-3'-ylacetonitrile Chemical group C=1C(CC#N)=CC=C2C=1C=CC1=CC=CC=C1C21OCCO1 KTAVNNANNXIHFO-UHFFFAOYSA-N 0.000 claims 1
KJPWWNLJWUIDGN-UHFFFAOYSA-N 2-spiro[1,3-dioxolane-2,11'-dibenzo[1,2-a:1',2'-e][7]annulene]-3'-ylpropanoic acid Chemical group C=1C(C(C(O)=O)C)=CC=C2C=1C=CC1=CC=CC=C1C21OCCO1 KJPWWNLJWUIDGN-UHFFFAOYSA-N 0.000 claims 1
235000019439 ethyl acetate Nutrition 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000000284 extract Substances 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 12
150000002825 nitriles Chemical class 0.000 description 11
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
235000019260 propionic acid Nutrition 0.000 description 10
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 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 7
230000002378 acidificating effect Effects 0.000 description 6
OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000003125 aqueous solvent Substances 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
150000004715 keto acids Chemical class 0.000 description 5
FZRKAZHKEDOPNN-UHFFFAOYSA-N Nitric oxide anion Chemical compound O=[N-] FZRKAZHKEDOPNN-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
238000005907 ketalization reaction Methods 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
206010061218 Inflammation Diseases 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
230000004054 inflammatory process Effects 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
NCLHNDGKDCGRTH-UHFFFAOYSA-M (2-methoxycarbonylphenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].COC(=O)C1=CC=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NCLHNDGKDCGRTH-UHFFFAOYSA-M 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
GXHPHMVJFXFRPH-UHFFFAOYSA-N 2-[2-(3-ethylphenyl)ethyl]benzoic acid Chemical compound CCC1=CC=CC(CCC=2C(=CC=CC=2)C(O)=O)=C1 GXHPHMVJFXFRPH-UHFFFAOYSA-N 0.000 description 2
BFRQZDHFAPHJIJ-UHFFFAOYSA-N 3-(bromomethyl)dibenzo[1,2-a:1',2'-e][7]annulen-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=CC=C(CBr)C=C21 BFRQZDHFAPHJIJ-UHFFFAOYSA-N 0.000 description 2
DWXOFJILZCSGJI-UHFFFAOYSA-N 3-methyl-5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=C(C)C=C12 DWXOFJILZCSGJI-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
230000004968 inflammatory condition Effects 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
150000002576 ketones Chemical group 0.000 description 2
239000010410 layer Substances 0.000 description 2
OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
230000035935 pregnancy Effects 0.000 description 2
238000003797 solvolysis reaction Methods 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
BJJYDCMOGPBBOM-UHFFFAOYSA-N 2-[2-(3-methylphenyl)ethenyl]benzoic acid Chemical compound CC1=CC=CC(C=CC=2C(=CC=CC=2)C(O)=O)=C1 BJJYDCMOGPBBOM-UHFFFAOYSA-N 0.000 description 1
UYRQLSZMCVITLP-UHFFFAOYSA-N 2-[2-(3-methylphenyl)ethyl]benzoic acid Chemical compound CC1=CC=CC(CCC=2C(=CC=CC=2)C(O)=O)=C1 UYRQLSZMCVITLP-UHFFFAOYSA-N 0.000 description 1
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
LLYXUFQXCNIGDG-UHFFFAOYSA-N 3-ethylbenzaldehyde Chemical compound CCC1=CC=CC(C=O)=C1 LLYXUFQXCNIGDG-UHFFFAOYSA-N 0.000 description 1
OIPXTYYPPAEXAL-UHFFFAOYSA-N 3-methyldibenzo[1,2-a:1',2'-e][7]annulen-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=CC=C(C)C=C21 OIPXTYYPPAEXAL-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
101100448366 Arabidopsis thaliana GH3.12 gene Proteins 0.000 description 1
101100129007 Arabidopsis thaliana LTD gene Proteins 0.000 description 1
208000010392 Bone Fractures Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
201000005569 Gout Diseases 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
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
208000006670 Multiple fractures Diseases 0.000 description 1
101100505385 Mus musculus Gpd1 gene Proteins 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
208000010040 Sprains and Strains Diseases 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
HJCMMOODWZOXML-UHFFFAOYSA-N bromo hypobromite Chemical compound BrOBr HJCMMOODWZOXML-UHFFFAOYSA-N 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
XHRNQDMNINGCES-UHFFFAOYSA-N cyclohept-4-en-1-one Chemical compound O=C1CCC=CCC1 XHRNQDMNINGCES-UHFFFAOYSA-N 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000007269 dehydrobromination reaction Methods 0.000 description 1
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
210000003754 fetus Anatomy 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
WVWZECQNFWFVFW-UHFFFAOYSA-N methyl 2-methylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C WVWZECQNFWFVFW-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
210000003205 muscle Anatomy 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
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/373—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in doubly bound form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/86—Unsaturated compounds containing keto groups containing six-membered aromatic rings and other 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
- C07C63/33—Polycyclic acids
- C07C63/331—Polycyclic acids with all carboxyl groups bound to non-condensed 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
- C07C63/66—Polycyclic acids with unsaturation outside the aromatic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO753418A 1975-09-08 1975-10-09 NO753418L (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/611,057 US3979430A (en)	1975-09-08	1975-09-08	Solvolytic process for the preparation of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic, propionic and butyric acids

Publications (1)

Publication Number	Publication Date
NO753418L true NO753418L (fr)	1977-03-09

Family

ID=24447448

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO753418A NO753418L (fr)	1975-09-08	1975-10-09

Country Status (5)

Country	Link
US (1)	US3979430A (fr)
DK (1)	DK468375A (fr)
FI (1)	FI752870A7 (fr)
NO (1)	NO753418L (fr)
SE (1)	SE7510936L (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4107322A (en) *	1976-06-03	1978-08-15	American Hoechst Corporation	Benzyl and related esters of 6,11-dihydrodibenz[b,e]oxepin-acetic acids
US4051149A (en) *	1976-06-18	1977-09-27	Syntex (U.S.A.) Inc.	6,11-Dihydrodibenzo-[b.e.]-thiepin-11-one-3-acetonitrile
DE2708189C2 (de) *	1977-02-25	1985-07-04	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von Phenylglyoxylsäureestern

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3270067A (en) *	1962-07-12	1966-08-30	Merck & Co Inc	Chemical process and products produced thereby
US3317582A (en) *	1962-07-18	1967-05-02	Merck & Co Inc	Dibenzocycloheptene compounds and processes for preparing the same
CH450398A (de) *	1964-02-18	1968-01-31	Hoffmann La Roche	Verfahren zur Herstellung von Dibenzocycloheptatrienverbindungen
US3580943A (en) *	1968-09-03	1971-05-25	Dow Chemical Co	Dibenzocycloheptene derivatives
US3649692A (en) *	1969-05-01	1972-03-14	Ayerst Mckenna & Harrison	4-amino alkyl-5-methylene-dibenzo-cycloheptenes and salts thereof

1975
- 1975-09-08 US US05/611,057 patent/US3979430A/en not_active Expired - Lifetime
- 1975-09-30 SE SE7510936A patent/SE7510936L/xx unknown
- 1975-10-09 NO NO753418A patent/NO753418L/no unknown
- 1975-10-15 FI FI752870A patent/FI752870A7/fi not_active Application Discontinuation
- 1975-10-17 DK DK468375A patent/DK468375A/da unknown

Also Published As

Publication number	Publication date
SE7510936L (sv)	1977-03-09
US3979430A (en)	1976-09-07
DK468375A (da)	1977-03-09
FI752870A7 (fr)	1977-03-09

Publication	Publication Date	Title
US3641127A (en)	1972-02-08	(3-benzoylphenyl) alkanoic acids
JP2556821B2 (ja)	1996-11-27	三環式芳香族化合物
US3829453A (en)	1974-08-13	Octahydroanthracene-2-aminoacetic acids and esters and mixed anhydrides thereof
US3839431A (en)	1974-10-01	Cyclopropylmethylphenylacetic acids and derivatives
DK149230B (da)	1986-03-24	Analogifremgangsmaade til fremstilling af 5-benzoyl-6-hydroxy-indan-1-carboxylsyrederivater eller farmaceutisk acceptable salte deraf
US4659728A (en)	1987-04-21	Hydroxy substituted 4,5-diphenyl-2-oxazole propanoic acid
US3979430A (en)	1976-09-07	Solvolytic process for the preparation of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic, propionic and butyric acids
EP0138765B1 (fr)	1989-08-16	Dérivés de 4H-benzo[4,5]cyclohepta[1,2-b]thiophène
SU1039439A3 (ru)	1983-08-30	Способ получени 2-(3-феноксифенил)-пропионовой кислоты или ее кальциевой соли
US4054579A (en)	1977-10-18	Intermediates in the process for the preparation of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic, propionic and butyric acids
EP0060445B1 (fr)	1984-08-01	Procédé de résolution de racémates, et lactonesters employés dans ce procédé
NO751401L (fr)	1975-10-23
US2966509A (en)	1960-12-27	New phenacylamines and process
JPS63290873A (ja)	1988-11-28	４−アミノ−６−フルオロクロマン−４−カルボン酸エステルおよびその誘導体
US4011241A (en)	1977-03-08	An intermediate in the preparation of 2-(5H-dibenzo[a,d]cyclophepten-5-on-2-yl)acetic, propionic and butyric acids
HU214086B (en)	1997-12-29	Process for producing 3-isoxazolecarboxylic acid and intermediates thereof
JP2549997B2 (ja)	1996-10-30	新規ハロケタール化合物
US3872112A (en)	1975-03-18	Tetrahydrofurfuryl aminoesters
US3829474A (en)	1974-08-13	5,5-diphenylpent-4-enoic acids and related compounds
US4124596A (en)	1978-11-07	Thienothienylcarbonyl-phenylalkanoic acids and derivatives thereof
NO120733B (fr)	1970-11-30
NO783589L (no)	1974-09-03	Analogifremgangsmaate for fremstilling av nye derivater av dibenzo(a,d)cyklohepten
JPH0129793B2 (fr)	1989-06-14
NO132199B (fr)	1975-06-23
KR790001825B1 (ko)	1979-12-22	스틸벤 유도체의 제조법