SU793394A3 - Способ получени замещенных нафто (2,3-в)пиран-2-карбоновых кислот или их солей - Google Patents

Способ получени замещенных нафто (2,3-в)пиран-2-карбоновых кислот или их солей Download PDF

Info

Publication number: SU793394A3
Authority: SU; USSR - Soviet Union
Prior art keywords: tetrahydro; solution; oxo; water; mixture
Prior art date: 1974-11-30

Application number

SU752191857A

Other languages

English (en)

Russian (ru)

Inventor

Чарльз Браун Роджер

Хазард Ричард

Мэнн Джон

Original Assignee

Физонз Лимитед (Фирма)

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.)

1974-11-30

Filing date

1975-11-27

Publication date

1980-12-30

1974-11-30 Priority claimed from GB51944/74A external-priority patent/GB1517153A/en

1975-11-27 Application filed by Физонз Лимитед (Фирма) filed Critical Физонз Лимитед (Фирма)

1980-12-30 Application granted granted Critical

1980-12-30 Publication of SU793394A3 publication Critical patent/SU793394A3/ru

Links

238000000034 method Methods 0.000 title claims description 26
150000003839 salts Chemical class 0.000 title claims description 10
CRLWVGQKDUMUBC-UHFFFAOYSA-N 10aH-benzo[g]chromene-2-carboxylic acid Chemical class C1=C2C=CC=CC2=CC2C1=CC=C(C(=O)O)O2 CRLWVGQKDUMUBC-UHFFFAOYSA-N 0.000 title description 2
239000000243 solution Substances 0.000 claims description 129
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 108
239000000047 product Substances 0.000 claims description 108
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 108
239000000203 mixture Substances 0.000 claims description 91
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 84
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 82
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 78
QFZTUWOWMRNMAH-UHFFFAOYSA-N 2h-pyran-2-carboxylic acid Chemical compound OC(=O)C1OC=CC=C1 QFZTUWOWMRNMAH-UHFFFAOYSA-N 0.000 claims description 56
239000007787 solid Substances 0.000 claims description 56
150000001875 compounds Chemical class 0.000 claims description 53
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 52
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 45
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
239000003921 oil Substances 0.000 claims description 42
235000019198 oils Nutrition 0.000 claims description 42
239000011734 sodium Substances 0.000 claims description 41
229910052708 sodium Inorganic materials 0.000 claims description 40
239000002253 acid Substances 0.000 claims description 35
238000010992 reflux Methods 0.000 claims description 33
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 claims description 32
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
239000000706 filtrate Substances 0.000 claims description 24
239000011541 reaction mixture Substances 0.000 claims description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
235000017557 sodium bicarbonate Nutrition 0.000 claims description 21
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 20
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims description 19
150000002148 esters Chemical class 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
239000010410 layer Substances 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 18
239000002244 precipitate Substances 0.000 claims description 18
159000000000 sodium salts Chemical class 0.000 claims description 18
238000005481 NMR spectroscopy Methods 0.000 claims description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 16
238000001816 cooling Methods 0.000 claims description 16
239000000284 extract Substances 0.000 claims description 16
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 14
238000004949 mass spectrometry Methods 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 14
-1 2-hydroxy-3-propyl Chemical group 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
238000002844 melting Methods 0.000 claims description 13
238000003756 stirring Methods 0.000 claims description 13
230000008018 melting Effects 0.000 claims description 12
239000003208 petroleum Substances 0.000 claims description 12
239000000843 powder Substances 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
229910052943 magnesium sulfate Inorganic materials 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
229960000583 acetic acid Drugs 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 10
238000001704 evaporation Methods 0.000 claims description 10
230000008020 evaporation Effects 0.000 claims description 10
235000019341 magnesium sulphate Nutrition 0.000 claims description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
239000000427 antigen Substances 0.000 claims description 8
102000036639 antigens Human genes 0.000 claims description 8
108091007433 antigens Proteins 0.000 claims description 8
239000012259 ether extract Substances 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 8
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
JMPLHIMPUGYSDQ-UHFFFAOYSA-M O1C(C=CC=C1)C(=O)[O-].[Na+] Chemical compound O1C(C=CC=C1)C(=O)[O-].[Na+] JMPLHIMPUGYSDQ-UHFFFAOYSA-M 0.000 claims description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
229910052783 alkali metal Chemical group 0.000 claims description 7
150000001340 alkali metals Chemical group 0.000 claims description 7
239000007864 aqueous solution Substances 0.000 claims description 7
238000007363 ring formation reaction Methods 0.000 claims description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
238000001914 filtration Methods 0.000 claims description 6
239000012362 glacial acetic acid Substances 0.000 claims description 6
239000012074 organic phase Substances 0.000 claims description 6
230000000144 pharmacologic effect Effects 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 5
239000013078 crystal Substances 0.000 claims description 5
238000002425 crystallisation Methods 0.000 claims description 5
230000008025 crystallization Effects 0.000 claims description 5
QJLUEXIEULPDNL-UHFFFAOYSA-L disodium 2H-pyran-2-carboxylate Chemical compound C1=CC(OC=C1)C(=O)[O-].C1=CC(OC=C1)C(=O)[O-].[Na+].[Na+] QJLUEXIEULPDNL-UHFFFAOYSA-L 0.000 claims description 5
238000001035 drying Methods 0.000 claims description 5
239000007789 gas Substances 0.000 claims description 5
230000007935 neutral effect Effects 0.000 claims description 5
239000011780 sodium chloride Substances 0.000 claims description 5
TVEZOBZJVCNKJM-UHFFFAOYSA-N 1-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)propan-1-one Chemical compound C1CCCC2=C1C=C(C(=O)CC)C(O)=C2 TVEZOBZJVCNKJM-UHFFFAOYSA-N 0.000 claims description 4
JRMAQQQTXDJDNC-UHFFFAOYSA-N 2-ethoxy-2-oxoacetic acid Chemical compound CCOC(=O)C(O)=O JRMAQQQTXDJDNC-UHFFFAOYSA-N 0.000 claims description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
206010020751 Hypersensitivity Diseases 0.000 claims description 4
238000004566 IR spectroscopy Methods 0.000 claims description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
230000007815 allergy Effects 0.000 claims description 4
238000004458 analytical method Methods 0.000 claims description 4
239000008346 aqueous phase Substances 0.000 claims description 4
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
238000000354 decomposition reaction Methods 0.000 claims description 4
VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 claims description 4
239000005457 ice water Substances 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
239000012044 organic layer Substances 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
238000001953 recrystallisation Methods 0.000 claims description 4
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims description 4
239000012258 stirred mixture Substances 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
PJPYEBKHGBAWMX-UHFFFAOYSA-N 1-(4-bromo-3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone Chemical compound C1CCCC2=C1C=C(C(=O)C)C(O)=C2Br PJPYEBKHGBAWMX-UHFFFAOYSA-N 0.000 claims description 3
OJTVEOFVZUESBT-UHFFFAOYSA-N 7-methoxy-2,2-dimethyl-3,4-dihydrochromen-5-ol Chemical compound C1CC(C)(C)OC2=CC(OC)=CC(O)=C21 OJTVEOFVZUESBT-UHFFFAOYSA-N 0.000 claims description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 3
238000010521 absorption reaction Methods 0.000 claims description 3
150000001336 alkenes Chemical class 0.000 claims description 3
208000010668 atopic eczema Diseases 0.000 claims description 3
239000002585 base Substances 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
238000005406 washing Methods 0.000 claims description 3
BOZLTXAJYKSLAI-UHFFFAOYSA-N 1-(2-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)ethanone Chemical compound C1CCCC2=C1C=CC(O)=C2C(=O)C BOZLTXAJYKSLAI-UHFFFAOYSA-N 0.000 claims description 2
LZMUYDQAVFZRSL-UHFFFAOYSA-N 1-(3-hydroxy-4-propyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone Chemical compound C1CCCC2=C1C=C(C(C)=O)C(O)=C2CCC LZMUYDQAVFZRSL-UHFFFAOYSA-N 0.000 claims description 2
HIOGQCOVPOXABP-UHFFFAOYSA-N 1-ethyl-5,6,7,8-tetrahydronaphthalen-2-ol Chemical compound C1CCCC2=C1C=CC(O)=C2CC HIOGQCOVPOXABP-UHFFFAOYSA-N 0.000 claims description 2
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 2
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 2
ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 2
LAGIJQKWXSGCHP-UHFFFAOYSA-N 7-methoxy-4-methyl-2,3-dihydrochromen-4-ol Chemical compound O1CCC(O)(C)C=2C1=CC(OC)=CC=2 LAGIJQKWXSGCHP-UHFFFAOYSA-N 0.000 claims description 2
IDRSZYOJAWDVSG-UHFFFAOYSA-N 7-methoxy-4-methyl-2h-chromene Chemical compound CC1=CCOC2=CC(OC)=CC=C21 IDRSZYOJAWDVSG-UHFFFAOYSA-N 0.000 claims description 2
229910015900 BF3 Inorganic materials 0.000 claims description 2
KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 2
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 claims description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
241001465754 Metazoa Species 0.000 claims description 2
235000019502 Orange oil Nutrition 0.000 claims description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
208000024780 Urticaria Diseases 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
201000009961 allergic asthma Diseases 0.000 claims description 2
230000000172 allergic effect Effects 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
235000019270 ammonium chloride Nutrition 0.000 claims description 2
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 claims description 2
230000037396 body weight Effects 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
239000002026 chloroform extract Substances 0.000 claims description 2
229940061627 chloromethyl methyl ether Drugs 0.000 claims description 2
150000004777 chromones Chemical class 0.000 claims description 2
238000007796 conventional method Methods 0.000 claims description 2
239000012043 crude product Substances 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
150000004683 dihydrates Chemical class 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
201000010099 disease Diseases 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
239000002024 ethyl acetate extract Substances 0.000 claims description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 2
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
201000001371 inclusion conjunctivitis Diseases 0.000 claims description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
239000011777 magnesium Substances 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 2
150000004702 methyl esters Chemical class 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000010502 orange oil Substances 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 2
229920000137 polyphosphoric acid Polymers 0.000 claims description 2
229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
230000008707 rearrangement Effects 0.000 claims description 2
239000004576 sand Substances 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
230000035945 sensitivity Effects 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
239000012312 sodium hydride Substances 0.000 claims description 2
229910000104 sodium hydride Inorganic materials 0.000 claims description 2
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 2
206010044325 trachoma Diseases 0.000 claims description 2
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
RRWHGEURWOVQRB-UHFFFAOYSA-N 1-[4-(chloromethyl)-3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl]ethanone Chemical compound C1CCCC2=C1C=C(C(=O)C)C(O)=C2CCl RRWHGEURWOVQRB-UHFFFAOYSA-N 0.000 claims 1
HLLSOEKIMZEGFV-UHFFFAOYSA-N 4-(dibutylsulfamoyl)benzoic acid Chemical compound CCCCN(CCCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 HLLSOEKIMZEGFV-UHFFFAOYSA-N 0.000 claims 1
DISYDHABSCTQFK-UHFFFAOYSA-N 7-methoxy-2,3-dihydrochromen-4-one Chemical compound O=C1CCOC2=CC(OC)=CC=C21 DISYDHABSCTQFK-UHFFFAOYSA-N 0.000 claims 1
KTSMDFCWNABPSP-UHFFFAOYSA-N 7-methoxy-4-methyl-3,4-dihydro-2h-chromene Chemical compound CC1CCOC2=CC(OC)=CC=C21 KTSMDFCWNABPSP-UHFFFAOYSA-N 0.000 claims 1
235000006693 Cassia laevigata Nutrition 0.000 claims 1
201000004624 Dermatitis Diseases 0.000 claims 1
239000007832 Na2SO4 Substances 0.000 claims 1
206010037660 Pyrexia Diseases 0.000 claims 1
241000735631 Senna pendula Species 0.000 claims 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 1
PYQQLJUXVKZOPJ-UHFFFAOYSA-K [B+3].[Cl-].[Cl-].[Cl-] Chemical compound [B+3].[Cl-].[Cl-].[Cl-] PYQQLJUXVKZOPJ-UHFFFAOYSA-K 0.000 claims 1
125000005605 benzo group Chemical group 0.000 claims 1
229950011260 betanaphthol Drugs 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
239000003610 charcoal Substances 0.000 claims 1
239000006071 cream Substances 0.000 claims 1
MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims 1
239000012024 dehydrating agents‎ Substances 0.000 claims 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
230000002496 gastric effect Effects 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
230000000968 intestinal effect Effects 0.000 claims 1
229910000372 mercury(II) sulfate Inorganic materials 0.000 claims 1
239000008267 milk Substances 0.000 claims 1
210000004080 milk Anatomy 0.000 claims 1
235000013336 milk Nutrition 0.000 claims 1
239000011259 mixed solution Substances 0.000 claims 1
239000012299 nitrogen atmosphere Substances 0.000 claims 1
229910052763 palladium Inorganic materials 0.000 claims 1
LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 claims 1
230000004044 response Effects 0.000 claims 1
238000006748 scratching Methods 0.000 claims 1
230000002393 scratching effect Effects 0.000 claims 1
229940124513 senna glycoside Drugs 0.000 claims 1
229910052938 sodium sulfate Inorganic materials 0.000 claims 1
235000011152 sodium sulphate Nutrition 0.000 claims 1
NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 claims 1
239000000725 suspension Substances 0.000 claims 1
230000008961 swelling Effects 0.000 claims 1
238000004809 thin layer chromatography Methods 0.000 claims 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DLKZWVIRKURGIR-UHFFFAOYSA-N 4-oxo-10-propyl-6,7,8,9-tetrahydrobenzo[g]chromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C(CCC)=C1CCCCC1=C2 DLKZWVIRKURGIR-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
LNZONKXKXBWZDQ-UHFFFAOYSA-N 1-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone Chemical compound C1CCCC2=C1C=C(C(=O)C)C(O)=C2 LNZONKXKXBWZDQ-UHFFFAOYSA-N 0.000 description 1
OXPOCXYMBUQEBH-UHFFFAOYSA-N 1-(7-hydroxy-4-methyl-3,4-dihydro-2h-chromen-6-yl)ethanone Chemical compound OC1=C(C(C)=O)C=C2C(C)CCOC2=C1 OXPOCXYMBUQEBH-UHFFFAOYSA-N 0.000 description 1
UOZNGGLOBFTUOV-UHFFFAOYSA-N 1-(7-methoxy-4-methyl-3,4-dihydro-2h-chromen-6-yl)ethanone Chemical compound O1CCC(C)C2=C1C=C(OC)C(C(C)=O)=C2 UOZNGGLOBFTUOV-UHFFFAOYSA-N 0.000 description 1
NTINDULSIUQKKT-UHFFFAOYSA-N 10-bromo-4-oxo-6,7,8,9-tetrahydrobenzo[g]chromene-2-carboxylic acid Chemical compound C1CCCC2=C1C=C1C(=O)C=C(C(=O)O)OC1=C2Br NTINDULSIUQKKT-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
ASCHDAQPKVWZJM-UHFFFAOYSA-N 4H-benzo[g]chromene-2-carboxylic acid Chemical compound O1C2=C(CC=C1C(=O)O)C=C1C=CC=CC1=C2 ASCHDAQPKVWZJM-UHFFFAOYSA-N 0.000 description 1
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
229910000497 Amalgam Inorganic materials 0.000 description 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
206010012434 Dermatitis allergic Diseases 0.000 description 1
208000009793 Milk Hypersensitivity Diseases 0.000 description 1
201000010859 Milk allergy Diseases 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
QLNKJGRLLJHPGT-UHFFFAOYSA-N ethyl 10-formyl-4-oxo-6,7,8,9-tetrahydrobenzo[g]chromene-2-carboxylate Chemical compound C1CCCC2=C1C=C1C(=O)C=C(C(=O)OCC)OC1=C2C=O QLNKJGRLLJHPGT-UHFFFAOYSA-N 0.000 description 1
XDVPRNCVGOQUIZ-UHFFFAOYSA-N ethyl 4-oxo-10-propyl-6,7,8,9-tetrahydrobenzo[g]chromene-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C2=C1C(CCC)=C1CCCCC1=C2 XDVPRNCVGOQUIZ-UHFFFAOYSA-N 0.000 description 1
VUJIZSLLFLNDIM-UHFFFAOYSA-N ethyl 5-hydroxy-4-oxo-10-propyl-6,7,8,9-tetrahydrobenzo[g]chromene-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C2=C1C(CCC)=C1CCCCC1=C2O VUJIZSLLFLNDIM-UHFFFAOYSA-N 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
201000005298 gastrointestinal allergy Diseases 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
KVHRJWIPNZSQAC-UHFFFAOYSA-N methyl 10-ethyl-4-oxo-6,7,8,9-tetrahydrobenzo[g]chromene-2-carboxylate Chemical compound O1C(C(=O)OC)=CC(=O)C2=C1C(CC)=C1CCCCC1=C2 KVHRJWIPNZSQAC-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
235000020681 well water Nutrition 0.000 description 1
239000002349 well water Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU752191857A 1974-11-30 1975-11-27 Способ получени замещенных нафто (2,3-в)пиран-2-карбоновых кислот или их солей SU793394A3 (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB51944/74A GB1517153A (en)	1974-11-30	1974-11-30	Naphthopyran-and benzodipyran-2-carboxylic acids and derivatives thereof
GB2104375		1975-05-16

Publications (1)

Publication Number	Publication Date
SU793394A3 true SU793394A3 (ru)	1980-12-30

Family

ID=26255067

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SU752191857A SU793394A3 (ru)	1974-11-30	1975-11-27	Способ получени замещенных нафто (2,3-в)пиран-2-карбоновых кислот или их солей
SU762377398A SU622402A3 (ru)	1974-11-30	1976-07-05	Способ получени замещенных6,7,8,9-тетрагидро4-оксо-10-алкил-4-нафто/2,3- /пиран 2-карбоновых кислот или их солей или их эфиров

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SU762377398A SU622402A3 (ru)	1974-11-30	1976-07-05	Способ получени замещенных6,7,8,9-тетрагидро4-оксо-10-алкил-4-нафто/2,3- /пиран 2-карбоновых кислот или их солей или их эфиров

Country Status (2)

Country	Link
CS (1)	CS191997B2 (cs)
SU (2)	SU793394A3 (cs)

1975
- 1975-11-21 CS CS131477A patent/CS191997B2/cs unknown
- 1975-11-27 SU SU752191857A patent/SU793394A3/ru active
1976
- 1976-07-05 SU SU762377398A patent/SU622402A3/ru active

Also Published As

Publication number	Publication date
CS191997B2 (en)	1979-07-31
SU622402A3 (ru)	1978-08-30

Publication	Publication Date	Title
SU1272984A3 (ru)	1986-11-23	Способ получени производных фталазин-4-ил-уксусной кислоты или их солей
US3484445A (en)	1969-12-16	Derivatives of chromone-2-carboxylic acid
JPS59161346A (ja)	1984-09-12	フエノール誘導体の製造法
US4474787A (en)	1984-10-02	7,6 Dioxo-4H,6H-pyrano[3,2-g]quinoline dicarboxylic acids and anti-allergic use thereof
EP0101330B1 (en)	1988-08-24	2-quinolone derivatives
CH533098A (fr)	1973-01-31	Procédé de préparation de benzopyrones
US3786071A (en)	1974-01-15	Chemical compounds chromone-2-carboxylic acids
SU793394A3 (ru)	1980-12-30	Способ получени замещенных нафто (2,3-в)пиран-2-карбоновых кислот или их солей
EP0190298B1 (en)	1989-10-18	4-(isoxazolyl)-thiazole-2-oxamic acids and derivatives thereof
US4698345A (en)	1987-10-06	Quinoline derivatives and their use as anti-asthmatic agents
SU1083909A3 (ru)	1984-03-30	Способ получени 6-замещенных производных пиранона
EP0014079B1 (en)	1981-11-18	Spiro-quinolylhydantoins, process for their preparation and pharmaceutical compositions thereof
US4335048A (en)	1982-06-15	5-(2-Hydroxypropoxy)-8-propyl-4H-1-benzopyran-4-one-2-carboxylic acid
DD219765A5 (de)	1985-03-13	Verfahren zur herstellung von substituierten hexahydropyrrolo (-1,2-a)-chinolin-, hexahydro-1h-pyrido (1,2-a)chinolin-, hexahydrobenzo(e)inden- und octahydrophenanthren-zns-mitteln
CA1205474A (en)	1986-06-03	Benzisoxazole carboxylic acids
JPS6045199B2 (ja)	1985-10-08	新規なイミダゾベンゾオキサジン及びそれらを含む製薬組成物
EP0150966B1 (en)	1989-07-12	Benzopyran derivatives, compositions containing them and processes for their preparation
US3860617A (en)	1975-01-14	Benzopyrans
NO743135L (cs)	1975-04-07
US3952104A (en)	1976-04-20	Benzopyran-2-carboxylic acids in the prevention of asthmatic symptoms
CA1230123A (en)	1987-12-08	3-alkyl-8-chloro-5,6-dihydrofuro-¬3,2-f\|-1,2- benzisoxazole-6-carboxylic acids
JPH0122276B2 (cs)	1989-04-25
US4228173A (en)	1980-10-14	Thiopyrano-benzopyrans, compositions and method of use thereof
US4258211A (en)	1981-03-24	4-Aminoaliphatic-2,3,5,6-[dibenzobicyclo[5.1.0]octanes] and salts thereof
US4670452A (en)	1987-06-02	Dioxo dibenzopyrans and anti-allergic use thereof