NO772604L - Fremgangsm}te for fremstilling av derivater av fenoksyhydroksypropylamin - Google Patents

Fremgangsm}te for fremstilling av derivater av fenoksyhydroksypropylamin

Info

Publication number: NO772604L
Authority: NO; Norway
Prior art keywords: formula; indicated; ether; phenoxy; title compound
Prior art date: 1976-07-22

Application number

NO77772604A

Other languages

English (en)

Norwegian (no)

Inventor

Jean-Marie Teulon

Original Assignee

Hexachimie

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.)

1976-07-22

Filing date

1977-07-21

Publication date

1978-01-24

1977-07-21 Application filed by Hexachimie filed Critical Hexachimie

1978-01-24 Publication of NO772604L publication Critical patent/NO772604L/no

Links

238000000034 method Methods 0.000 title claims description 12
LBSOXWCAEGGPDY-UHFFFAOYSA-N 3-(phenoxyamino)propan-1-ol Chemical class OCCCNOC1=CC=CC=C1 LBSOXWCAEGGPDY-UHFFFAOYSA-N 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 109
-1 alkyl radical Chemical class 0.000 claims description 28
239000002904 solvent Substances 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 16
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims description 2
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 description 2
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 178
239000013078 crystal Substances 0.000 description 86
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
238000002844 melting Methods 0.000 description 59
230000008018 melting Effects 0.000 description 59
239000000243 solution Substances 0.000 description 54
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 53
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
239000001294 propane Substances 0.000 description 49
239000011541 reaction mixture Substances 0.000 description 40
229910052739 hydrogen Inorganic materials 0.000 description 37
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 36
239000000203 mixture Substances 0.000 description 36
239000000047 product Substances 0.000 description 35
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
238000001953 recrystallisation Methods 0.000 description 25
239000003921 oil Substances 0.000 description 24
239000012071 phase Substances 0.000 description 22
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
238000001704 evaporation Methods 0.000 description 18
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
229910000029 sodium carbonate Inorganic materials 0.000 description 18
230000008020 evaporation Effects 0.000 description 17
239000000284 extract Substances 0.000 description 17
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 16
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 15
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 13
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 13
229910052938 sodium sulfate Inorganic materials 0.000 description 13
235000011152 sodium sulphate Nutrition 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 11
239000001257 hydrogen Substances 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
238000001816 cooling Methods 0.000 description 10
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 10
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
238000001914 filtration Methods 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
238000010992 reflux Methods 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
230000002378 acidificating effect Effects 0.000 description 7
239000003480 eluent Substances 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
238000001035 drying Methods 0.000 description 6
LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 6
229910000103 lithium hydride Inorganic materials 0.000 description 6
239000011976 maleic acid Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
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 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
239000004411 aluminium Substances 0.000 description 5
229910000091 aluminium hydride Inorganic materials 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000012230 colorless oil Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
150000002989 phenols Chemical class 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
239000011591 potassium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
PEJIZIIPFKEOTF-UHFFFAOYSA-N 4-(oxolan-2-ylmethyl)phenol Chemical compound C1=CC(O)=CC=C1CC1OCCC1 PEJIZIIPFKEOTF-UHFFFAOYSA-N 0.000 description 4
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
238000005727 Friedel-Crafts reaction Methods 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 4
229960002327 chloral hydrate Drugs 0.000 description 4
229910052736 halogen Chemical group 0.000 description 4
150000002367 halogens Chemical group 0.000 description 4
150000004678 hydrides Chemical class 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
150000001414 amino alcohols Chemical class 0.000 description 3
229930188620 butyrolactone Natural products 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
229960001317 isoprenaline Drugs 0.000 description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
SBBRYZNVKDXNSS-UHFFFAOYSA-N (4-methoxyphenyl)-(5-methylfuran-2-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(C)O1 SBBRYZNVKDXNSS-UHFFFAOYSA-N 0.000 description 2
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
QATGNZVUWGXOCE-UHFFFAOYSA-N 4-(furan-2-ylmethyl)phenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CO1 QATGNZVUWGXOCE-UHFFFAOYSA-N 0.000 description 2
PIAIYXKVEYUFPQ-UHFFFAOYSA-N 4-[(5-methylfuran-2-yl)methyl]phenol Chemical compound Cc1ccc(Cc2ccc(O)cc2)o1 PIAIYXKVEYUFPQ-UHFFFAOYSA-N 0.000 description 2
QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
NAPOUMOKYYYFRP-UHFFFAOYSA-N BrC1=C(C=CC(=C1)CC1CCCO1)O Chemical compound BrC1=C(C=CC(=C1)CC1CCCO1)O NAPOUMOKYYYFRP-UHFFFAOYSA-N 0.000 description 2
PDCPWIYTFQCYKL-UHFFFAOYSA-N C(CC)C1=C(C=CC(=C1)CC1CCCO1)O Chemical compound C(CC)C1=C(C=CC(=C1)CC1CCCO1)O PDCPWIYTFQCYKL-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
RQKWYHZGAGSCSV-UHFFFAOYSA-N ClC1=C(C=CC(=C1)CC1CCCO1)O Chemical compound ClC1=C(C=CC(=C1)CC1CCCO1)O RQKWYHZGAGSCSV-UHFFFAOYSA-N 0.000 description 2
238000005618 Fries rearrangement reaction Methods 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
230000017858 demethylation Effects 0.000 description 2
238000010520 demethylation reaction Methods 0.000 description 2
230000035487 diastolic blood pressure Effects 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 2
BGMIRDHBNWQSGE-UHFFFAOYSA-N hypochlorous acid;pyridine Chemical compound ClO.C1=CC=NC=C1 BGMIRDHBNWQSGE-UHFFFAOYSA-N 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
229940014800 succinic anhydride Drugs 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
MKYMYZJJFMPDOA-UHFFFAOYSA-N 1-(4-phenylmethoxyphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC1=CC=CC=C1 MKYMYZJJFMPDOA-UHFFFAOYSA-N 0.000 description 1
HVCFCNAITDHQFX-UHFFFAOYSA-N 1-cyclopropylethanone Chemical compound CC(=O)C1CC1 HVCFCNAITDHQFX-UHFFFAOYSA-N 0.000 description 1
RQUBLQRVLBWBLZ-UHFFFAOYSA-N 1-methoxy-2-propylbenzene Chemical compound CCCC1=CC=CC=C1OC RQUBLQRVLBWBLZ-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
ZVTWZSXLLMNMQC-UHFFFAOYSA-N 4-phenylmethoxybenzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 ZVTWZSXLLMNMQC-UHFFFAOYSA-N 0.000 description 1
241000269627 Amphiuma means Species 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
HNYPNSLPQXPHIB-UHFFFAOYSA-N C(CC)C1=C(C=CC(=C1)CC1=CC=CO1)O Chemical compound C(CC)C1=C(C=CC(=C1)CC1=CC=CO1)O HNYPNSLPQXPHIB-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
238000003512 Claisen condensation reaction Methods 0.000 description 1
238000005821 Claisen rearrangement reaction Methods 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
231100000111 LD50 Toxicity 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000700159 Rattus Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
239000000674 adrenergic antagonist Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
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 1
239000003795 chemical substances by application Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000004882 diastolic arterial blood pressure Effects 0.000 description 1
230000003205 diastolic effect Effects 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
150000004715 keto acids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
150000002680 magnesium Chemical class 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000001665 trituration Methods 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- 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
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D309/06—Radicals substituted by oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Pharmacology & Pharmacy (AREA)
Cardiology (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Furan Compounds (AREA)
Pyrane Compounds (AREA)

NO77772604A 1976-07-22 1977-07-21 Fremgangsm}te for fremstilling av derivater av fenoksyhydroksypropylamin NO772604L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB3064776		1976-07-22
GB5357676		1976-12-22

Publications (1)

Publication Number	Publication Date
NO772604L true NO772604L (no)	1978-01-24

Family

ID=26260544

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO77772604A NO772604L (no)	1976-07-22	1977-07-21	Fremgangsm}te for fremstilling av derivater av fenoksyhydroksypropylamin

Country Status (11)

Country	Link
JP (1)	JPS5312851A (da)
AU (1)	AU2714177A (da)
DE (1)	DE2733305A1 (da)
DK (1)	DK329577A (da)
ES (1)	ES460866A1 (da)
FR (1)	FR2359135A1 (da)
GR (1)	GR61995B (da)
NL (1)	NL7707949A (da)
NO (1)	NO772604L (da)
PT (1)	PT66781B (da)
SE (1)	SE7708368L (da)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS58160154U (ja) *	1983-03-01	1983-10-25	セイコーエプソン株式会社	印字装置
GB0319069D0 (en) *	2003-08-14	2003-09-17	Glaxo Group Ltd	Therapeutically useful compounds
EP1737809B1 (en)	2004-02-27	2013-09-18	Amgen, Inc	Compounds, pharmaceutical compositions and methods for use in treating metabolic disorders
US7465804B2 (en)	2005-05-20	2008-12-16	Amgen Inc.	Compounds, pharmaceutical compositions and methods for their use in treating metabolic disorders
US7582803B2 (en)	2005-09-14	2009-09-01	Amgen Inc.	Conformationally constrained 3-(4-hydroxy-phenyl)-substituted-propanoic acids useful for treating metabolic disorders
EP2061760A1 (en)	2006-09-07	2009-05-27	Amgen, Inc	Benzo-fused compounds for use in treating metabolic disorders
CA2662305C (en)	2006-09-07	2012-04-17	Amgen Inc.	Heterocyclic gpr40 modulators
ES2446419T3 (es)	2007-04-16	2014-03-07	Amgen, Inc	Moduladores de GPR40 de ácidos bifenilfenoxi, tiofenil y aminofenilpropanoico sustituidos
JP5591706B2 (ja)	2007-10-10	2014-09-17	アムジエン・インコーポレーテツド	置換ビフェニルｇｐｒ４０調節因子
WO2009111056A1 (en)	2008-03-06	2009-09-11	Amgen Inc.	Conformationally constrained carboxylic acid derivatives useful for treating metabolic disorders
AU2009303475B2 (en)	2008-10-15	2012-09-13	Amgen Inc.	Spirocyclic GPR40 modulators
AU2024413085A1 (en) *	2023-12-28	2026-08-13	Cytosinlab Therapeutics Co., Ltd.	Tdg inhibitor compound and use thereof

1977
- 1977-07-01 FR FR7720380A patent/FR2359135A1/fr not_active Withdrawn
- 1977-07-08 PT PT66781A patent/PT66781B/pt unknown
- 1977-07-09 GR GR53932A patent/GR61995B/el unknown
- 1977-07-15 NL NL7707949A patent/NL7707949A/xx not_active Application Discontinuation
- 1977-07-19 ES ES77460866A patent/ES460866A1/es not_active Expired
- 1977-07-19 AU AU27141/77A patent/AU2714177A/en active Pending
- 1977-07-20 SE SE7708368A patent/SE7708368L/xx unknown
- 1977-07-20 DK DK329577A patent/DK329577A/da unknown
- 1977-07-21 DE DE19772733305 patent/DE2733305A1/de active Pending
- 1977-07-21 NO NO77772604A patent/NO772604L/no unknown
- 1977-07-22 JP JP8826877A patent/JPS5312851A/ja active Pending

Also Published As

Publication number	Publication date
DE2733305A1 (de)	1978-01-26
PT66781B (fr)	1978-12-18
DK329577A (da)	1978-01-23
NL7707949A (nl)	1978-01-24
SE7708368L (sv)	1978-01-23
JPS5312851A (en)	1978-02-04
ES460866A1 (es)	1978-08-16
PT66781A (fr)	1977-08-01
AU2714177A (en)	1979-01-25
GR61995B (en)	1979-02-14
FR2359135A1 (fr)	1978-02-17

Publication	Publication Date	Title
DK143275B (da)	1981-08-03	Analogifremgangsmaade til fremstilling af 1-(3-dimethylaminopropyl)-phthalanderivater eller syreadditionssalte deraf
US20010041674A1 (en)	2001-11-15	C-glycosides and preparation of thereof as antidiabetic agents
NO171273B (no)	1992-11-09	Analogifremgangsmaate for fremstilling av terapeutisk aktive 5-arylalkyl-4-alkoksy-2(5h)-furanoner
DE2256004A1 (de)	1973-05-17	Substituierte benzofurane
PL139439B1 (en)	1987-01-31	Method of obtaining imidazoline derivatives
BG98867A (bg)	1995-03-31	Бензопиран и съответстващи му левкотриен в долу 4 антагонисти
EP0011426A1 (en)	1980-05-28	Halogen-substituted benzopyran- and benzothiopyran-4-carboxylic acids, their preparation and pharmaceutical compositions containing the same
DE2733305A1 (de)	1978-01-26	Neue phenoxyhydroxypropylamine, verfahren zu ihrer herstellung und ihre therapeutische anwendung
NO176099B (no)	1994-10-24	Analogifremgangsmåte for fremstilling av terapeutisk aktive 4-(2-okso-3-pyridyl)-kromanderivater
US5089654A (en)	1992-02-18	Chalcone derivatives
GB2056435A (en)	1981-03-18	Novel Tetrahydropyridine and Piperidine Substituted Benzofuranes and Related Compounds
CH464172A (fr)	1968-10-31	Procédé de préparation d'acides carboxyliques -substitués
HU199806B (en)	1990-03-28	Process for producing (d-cis)-1,3,4,5-tetrahydro-4-phenyl-2h-benzazepin-2-one derivatives
EP1740531A1 (en)	2007-01-10	Indene derivatives and process for the preparation thereof
HU211554A9 (en)	1995-12-28	Circulation-active dibenzo/1,5/dioxocin-5-ones
NO790948L (no)	1979-09-25	Fremggangsmaate for fremstilling av dilignolderivater
HU180916B (hu)	1983-05-30	Eljárás benzo[c]kinolin-származékok előállítására
Cristol et al.	1945	Dehydrochlorination of 1-trichloro-2-o-chlorophenyl-2-p-chlorophenylethane (o, p'-DDT isomer)
US5489592A (en)	1996-02-06	3,4-dihydro-4-oxo-3-(2-propenyl)-1-phthalazineacetic acids and derivatives, their preparations and medicines containing them
DE4115465A1 (de)	1992-11-12	Neue in 4-stellung durch aryl oder n-heteroaryl substituierte 2h-benzo(b)pyran-derivate, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen
US4432984A (en)	1984-02-21	Anti-hypertensive benzodioxan derivatives
CH685344A5 (fr)	1995-06-15	Dérivés de la benzofuranylimidazole, leur procédé de préparation ainsi qu'une composition thérapeutique les contenant.
JP2549997B2 (ja)	1996-10-30	新規ハロケタール化合物
US6552069B1 (en)	2003-04-22	3-methyl-chroman and -thiochroman derivatives
NO813446L (no)	1982-04-15	1,5-bis(1,4-benzodioksin-2yl)-3-azapentan-1,5-dioler, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse forbindelser samt deres terapeutiske anvendelse