CS235057B2 - Method of arylphenylnaphtalen derivatives production - Google Patents
Method of arylphenylnaphtalen derivatives production Download PDFInfo
- Publication number
- CS235057B2 CS235057B2 CS766971A CS697176A CS235057B2 CS 235057 B2 CS235057 B2 CS 235057B2 CS 766971 A CS766971 A CS 766971A CS 697176 A CS697176 A CS 697176A CS 235057 B2 CS235057 B2 CS 235057B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- mixture
- compounds
- methoxy
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 10
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 claims description 10
- -1 methoxy, benzyloxy Chemical group 0.000 claims description 8
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 claims description 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 4
- RBWRWAUAVRMBAC-UHFFFAOYSA-M magnesium;methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=[C-]C=C1 RBWRWAUAVRMBAC-UHFFFAOYSA-M 0.000 claims description 3
- KPIKJMHJFCSHEG-UHFFFAOYSA-N 1-(4-methoxybenzoyl)-3,4-dihydro-1h-naphthalen-2-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1C2=CC=CC=C2CCC1=O KPIKJMHJFCSHEG-UHFFFAOYSA-N 0.000 claims description 2
- KCKZIWSINLBROE-UHFFFAOYSA-N 3,4-dihydro-1h-naphthalen-2-one Chemical compound C1=CC=C2CC(=O)CCC2=C1 KCKZIWSINLBROE-UHFFFAOYSA-N 0.000 claims description 2
- ICZNPZGJAVCRIV-UHFFFAOYSA-N 6-methoxy-1-(4-phenylmethoxybenzoyl)-3,4-dihydro-1h-naphthalen-2-one Chemical compound O=C1CCC2=CC(OC)=CC=C2C1C(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 ICZNPZGJAVCRIV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 22
- 241001465754 Metazoa Species 0.000 abstract description 11
- 230000035558 fertility Effects 0.000 abstract description 9
- 150000003839 salts Chemical class 0.000 abstract description 7
- 239000001257 hydrogen Substances 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 241000124008 Mammalia Species 0.000 abstract description 3
- 241000607479 Yersinia pestis Species 0.000 abstract description 3
- 231100000252 nontoxic Toxicity 0.000 abstract description 3
- 230000003000 nontoxic effect Effects 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000003433 contraceptive agent Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 150000002790 naphthalenes Chemical class 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract 2
- 229940124558 contraceptive agent Drugs 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- 239000000203 mixture Substances 0.000 description 65
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 239000000047 product Substances 0.000 description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000002024 ethyl acetate extract Substances 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000003509 anti-fertility effect Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 5
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical class C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000004237 preparative chromatography Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000282421 Canidae Species 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 210000003754 fetus Anatomy 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000271566 Aves Species 0.000 description 3
- 239000002285 corn oil Substances 0.000 description 3
- 235000005687 corn oil Nutrition 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 230000035935 pregnancy Effects 0.000 description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- PANZFQYXPMCHFD-UHFFFAOYSA-N 2,3-diphenyl-1h-indene Chemical class C12=CC=CC=C2CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PANZFQYXPMCHFD-UHFFFAOYSA-N 0.000 description 2
- FRIGLBWVTJAEHM-UHFFFAOYSA-N 3,4-diphenyl-1,2-dihydronaphthalene Chemical class C1CC2=CC=CC=C2C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 FRIGLBWVTJAEHM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 239000002871 fertility agent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000013011 mating Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 230000003637 steroidlike Effects 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
- RBRKGVOEJOBIDZ-UHFFFAOYSA-N (4-hydroxyphenyl)-(2-phenyl-3,4-dihydronaphthalen-1-yl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)CCC2=CC=CC=C12 RBRKGVOEJOBIDZ-UHFFFAOYSA-N 0.000 description 1
- UNOQWPOQMYOWJF-UHFFFAOYSA-N (4-hydroxyphenyl)-[2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C1=CC=C(O)C=C1 UNOQWPOQMYOWJF-UHFFFAOYSA-N 0.000 description 1
- JHCMYSXRSMHYAX-UHFFFAOYSA-N (4-methoxyphenyl)-(2-phenyl-3,4-dihydronaphthalen-1-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)CCC2=CC=CC=C12 JHCMYSXRSMHYAX-UHFFFAOYSA-N 0.000 description 1
- CJEXERCBZDVOAT-UHFFFAOYSA-N (4-methoxyphenyl)-(2-phenylnaphthalen-1-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C=CC2=CC=CC=C12 CJEXERCBZDVOAT-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- NAVMNPSRQRDRRL-UHFFFAOYSA-N 1,2-dihydronaphthalen-1-yl(phenyl)methanone Chemical compound C1C=CC2=CC=CC=C2C1C(=O)C1=CC=CC=C1 NAVMNPSRQRDRRL-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- AWJXEUXVDUIDEV-UHFFFAOYSA-N 1-chloropyrrolidin-2-one Chemical compound ClN1CCCC1=O AWJXEUXVDUIDEV-UHFFFAOYSA-N 0.000 description 1
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 description 1
- HZEKNWNIWZKREL-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1,2-dihydronaphthalene Chemical class C1=CC(OC)=CC=C1C1=CC2=CC=CC=C2CC1 HZEKNWNIWZKREL-UHFFFAOYSA-N 0.000 description 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 1
- RMRKDYNVZWKAFP-UHFFFAOYSA-N 6-methoxy-3,4-dihydro-1h-naphthalen-2-one Chemical compound C1C(=O)CCC2=CC(OC)=CC=C21 RMRKDYNVZWKAFP-UHFFFAOYSA-N 0.000 description 1
- OAWCMXCTQPOKQN-UHFFFAOYSA-N 7-methoxy-1,2-dihydronaphthalene Chemical class C1=CCCC2=CC(OC)=CC=C21 OAWCMXCTQPOKQN-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- OMPIYDSYGYKWSG-UHFFFAOYSA-N Citronensaeure-alpha-aethylester Natural products CCOC(=O)CC(O)(C(O)=O)CC(O)=O OMPIYDSYGYKWSG-UHFFFAOYSA-N 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000287127 Passeridae Species 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- FCLZCOCSZQNREK-UHFFFAOYSA-N Pyrrolidine, hydrochloride Chemical compound Cl.C1CCNC1 FCLZCOCSZQNREK-UHFFFAOYSA-N 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- KRULEDWAJRZCIA-UHFFFAOYSA-N [6-methoxy-2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-(4-phenylmethoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC(OC)=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 KRULEDWAJRZCIA-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 229940057975 ethyl citrate Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- GJLNWLVPAHNBQN-UHFFFAOYSA-N phenyl 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OC1=CC=CC=C1 GJLNWLVPAHNBQN-UHFFFAOYSA-N 0.000 description 1
- BNZYBNYNPXKWCM-UHFFFAOYSA-N phenyl 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC1=CC=CC=C1 BNZYBNYNPXKWCM-UHFFFAOYSA-N 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- 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
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- 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
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
- C07C59/265—Citric acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62599175A | 1975-10-28 | 1975-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS235057B2 true CS235057B2 (en) | 1985-04-16 |
Family
ID=24508491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS766971A CS235057B2 (en) | 1975-10-28 | 1976-10-28 | Method of arylphenylnaphtalen derivatives production |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS6045191B2 (fr) |
| AR (1) | AR214622A1 (fr) |
| AT (1) | AT346321B (fr) |
| AU (1) | AU509372B2 (fr) |
| BE (1) | BE847716A (fr) |
| BG (1) | BG27555A3 (fr) |
| CA (1) | CA1078834A (fr) |
| CH (2) | CH624398A5 (fr) |
| CS (1) | CS235057B2 (fr) |
| DD (1) | DD127460A5 (fr) |
| DE (1) | DE2646213C2 (fr) |
| DK (1) | DK484776A (fr) |
| ES (1) | ES452735A1 (fr) |
| FR (1) | FR2329264A1 (fr) |
| GB (1) | GB1561687A (fr) |
| GR (1) | GR61816B (fr) |
| HU (1) | HU175227B (fr) |
| IE (1) | IE43641B1 (fr) |
| IL (1) | IL50772A (fr) |
| MX (1) | MX4291E (fr) |
| NL (1) | NL187164C (fr) |
| NZ (1) | NZ182421A (fr) |
| PH (1) | PH14538A (fr) |
| PL (2) | PL111987B1 (fr) |
| PT (1) | PT65752B (fr) |
| RO (1) | RO70755A (fr) |
| SE (1) | SE428689B (fr) |
| SU (2) | SU791220A3 (fr) |
| YU (1) | YU262276A (fr) |
| ZA (1) | ZA766439B (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4179558A (en) * | 1978-01-30 | 1979-12-18 | E. R. Squibb & Sons, Inc. | Naphthalenone derivatives and analogs |
| DE3121175A1 (de) * | 1981-05-27 | 1982-12-16 | Klinge Pharma GmbH, 8000 München | Erythro-1,2,3-triphenyl-1-pentanon-derivate sowie verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4410553A (en) | 1981-08-28 | 1983-10-18 | Mcginty James | Method and apparatus for cooking particulate foodstuffs |
| JPH0717589B2 (ja) * | 1990-01-22 | 1995-03-01 | ファイザー製薬株式会社 | 新規１，３―ジカルボニル化合物およびその組成物 |
| US6391892B1 (en) * | 1995-03-10 | 2002-05-21 | Eli Lilly And Company | Naphthyl pharmaceutical compounds |
-
1976
- 1976-10-13 DE DE2646213A patent/DE2646213C2/de not_active Expired
- 1976-10-20 MX MX764988U patent/MX4291E/es unknown
- 1976-10-21 CA CA263,896A patent/CA1078834A/fr not_active Expired
- 1976-10-21 NZ NZ182421A patent/NZ182421A/xx unknown
- 1976-10-22 GB GB43884/76A patent/GB1561687A/en not_active Expired
- 1976-10-22 PH PH19030A patent/PH14538A/en unknown
- 1976-10-25 PT PT65752A patent/PT65752B/pt unknown
- 1976-10-25 GR GR52004A patent/GR61816B/el unknown
- 1976-10-26 PL PL1976211453A patent/PL111987B1/pl unknown
- 1976-10-26 PL PL1976193264A patent/PL104551B1/pl unknown
- 1976-10-26 AU AU19004/76A patent/AU509372B2/en not_active Expired
- 1976-10-26 SU SU762414461A patent/SU791220A3/ru active
- 1976-10-26 ES ES452735A patent/ES452735A1/es not_active Expired
- 1976-10-26 RO RO7688227A patent/RO70755A/fr unknown
- 1976-10-26 JP JP51129305A patent/JPS6045191B2/ja not_active Expired
- 1976-10-27 HU HU76EI716A patent/HU175227B/hu unknown
- 1976-10-27 YU YU02622/76A patent/YU262276A/xx unknown
- 1976-10-27 SE SE7611953A patent/SE428689B/xx not_active IP Right Cessation
- 1976-10-27 ZA ZA00766439A patent/ZA766439B/xx unknown
- 1976-10-27 CH CH1355476A patent/CH624398A5/de not_active IP Right Cessation
- 1976-10-27 DK DK484776A patent/DK484776A/da not_active Application Discontinuation
- 1976-10-27 IL IL50772A patent/IL50772A/xx unknown
- 1976-10-27 IE IE2371/76A patent/IE43641B1/en unknown
- 1976-10-28 BE BE1007722A patent/BE847716A/fr not_active IP Right Cessation
- 1976-10-28 NL NLAANVRAGE7611974,A patent/NL187164C/xx not_active IP Right Cessation
- 1976-10-28 DD DD195507A patent/DD127460A5/xx unknown
- 1976-10-28 BG BG034552A patent/BG27555A3/xx unknown
- 1976-10-28 AT AT800576A patent/AT346321B/de not_active IP Right Cessation
- 1976-10-28 CS CS766971A patent/CS235057B2/cs unknown
- 1976-10-28 FR FR7632511A patent/FR2329264A1/fr active Granted
- 1976-10-28 AR AR265274A patent/AR214622A1/es active
-
1978
- 1978-07-25 SU SU782641053A patent/SU818476A3/ru active
-
1980
- 1980-08-28 CH CH648780A patent/CH624376A5/de not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4230862A (en) | Antifertility compounds | |
| CA1090795A (fr) | 2-phenyl-3-aroylbenzothiophenes et leurs 1-oxydes | |
| IL28643A (en) | History 1 - Phenyl - 2 - Aminoethanol | |
| US4323707A (en) | Antifertility compounds | |
| US3960911A (en) | Ferrocene compounds and preparation | |
| US3205136A (en) | Antidepressant phenyloxyalkylamines | |
| IE47960B1 (en) | Tetrazole derivatives | |
| JPH0227326B2 (fr) | ||
| US3940407A (en) | β-Adrenergic blocking agents in the 1,2,3-thiadiazole series | |
| US4075223A (en) | Novel antifertility agents | |
| US4400543A (en) | 3-Phenyl-4-benzoyl-1,2-dihydronaphthalenes | |
| CA1078834A (fr) | Compose contraceptif | |
| KR800000943B1 (ko) | 아로일-페닐나프탈렌 유도체의 제조방법 | |
| KR800000942B1 (ko) | 아로일-페닐나프탈렌 유도체의 제조방법 | |
| USRE28939E (en) | 3-Aminoindazole derivatives | |
| US4283404A (en) | Aroylethenylpiperidinobutyrophenone antipsychotic agents | |
| HU184791B (en) | Process for preparing derivatives of tetrahydro-pyrid-4-yl-indole | |
| US4454136A (en) | Substituted benzopyranotriazoles and antiallergic use | |
| JPS58177992A (ja) | イソキサゾ−ル−〔５，４−ｂ〕−ピリジン類 | |
| KR800000145B1 (ko) | 새로운 항 수정제의 제조방법 | |
| GB2142024A (en) | Terphenyl derivatives | |
| US4108896A (en) | Anthracene derivatives | |
| CA1055527A (fr) | Procedes pour la preparation de benzobicycloalkene amines et de composes connexes | |
| US3983124A (en) | Fluorene compounds | |
| CH646135A5 (fr) | Derives d'acides alpha-((aminomethylhydroxybenzoyl)-4-phenoxy disubstitue) alcanoiques et composition pharmaceutique les contenant. |