PL85433B1 - - Google Patents
Download PDFInfo
- Publication number
- PL85433B1 PL85433B1 PL1973164886A PL16488673A PL85433B1 PL 85433 B1 PL85433 B1 PL 85433B1 PL 1973164886 A PL1973164886 A PL 1973164886A PL 16488673 A PL16488673 A PL 16488673A PL 85433 B1 PL85433 B1 PL 85433B1
- Authority
- PL
- Poland
- Prior art keywords
- benzopyran
- mol
- solution
- carboxy
- general formula
- Prior art date
Links
- 239000000243 solution Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 29
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- -1 methoxy, acetyloxy Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- 238000010992 reflux Methods 0.000 description 17
- 239000007859 condensation product Substances 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000011734 sodium Substances 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 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 10
- 239000000725 suspension Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 208000010668 atopic eczema Diseases 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910006069 SO3H Chemical group 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- UXXOGXRLAYMMCY-UHFFFAOYSA-N 1-(3-hydroxy-6,6-dimethylbenzo[c]chromen-2-yl)ethanone Chemical compound C1=CC=C2C(C=C(C(=C3)O)C(=O)C)=C3OC(C)(C)C2=C1 UXXOGXRLAYMMCY-UHFFFAOYSA-N 0.000 description 1
- VUSSHPNHLDYLPY-UHFFFAOYSA-N 1-(8-chloro-3-hydroxy-6,6-dimethylbenzo[c]chromen-2-yl)ethanone Chemical compound ClC1=CC=C2C(C=C(C(=C3)O)C(=O)C)=C3OC(C)(C)C2=C1 VUSSHPNHLDYLPY-UHFFFAOYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 238000005618 Fries rearrangement reaction Methods 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 201000009053 Neurodermatitis Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- JMFAMSUOZFKZCD-UHFFFAOYSA-N acetic acid;methylsulfinylmethane Chemical compound CC(O)=O.CS(C)=O JMFAMSUOZFKZCD-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008023 pharmaceutical filler Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- WZODLFCLKIXWGA-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)C)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] WZODLFCLKIXWGA-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000012749 thinning agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrane Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT742572A AT320645B (de) | 1972-08-29 | 1972-08-29 | Verfahren zur Herstellung neuer 2-Carboxy-4-oxo-4H,10H-(2)-benzopyrano-[4,3-g]-(1)-benzopyrane und ihrer Salze |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL85433B1 true PL85433B1 (US20080293856A1-20081127-C00127.png) | 1976-04-30 |
Family
ID=3595927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973164886A PL85433B1 (US20080293856A1-20081127-C00127.png) | 1972-08-29 | 1973-08-28 |
Country Status (26)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5498419A (en) * | 1994-06-03 | 1996-03-12 | Pars; Harry G. | Fumarate salt of 4-(diethyl-3-(1-methyloctyl)-7,8,9,10-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol, 4-(diethyl-amino) butyric |
| US5892118A (en) * | 1996-10-09 | 1999-04-06 | Daiwa Kasei Industry Co., Ltd. | Process for producing 4,6-diaminoresorcinols |
| WO2004073612A2 (en) * | 2003-02-13 | 2004-09-02 | Merck & Co. Inc. | Estrogen receptor modulators |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3741990A (en) * | 1969-07-28 | 1973-06-26 | Upjohn Co | Organic compounds and processes |
-
1972
- 1972-08-29 AT AT742572A patent/AT320645B/de not_active IP Right Cessation
-
1973
- 1973-08-21 RO RO7300075862A patent/RO62920A/ro unknown
- 1973-08-21 RO RO7300078264A patent/RO63037A/ro unknown
- 1973-08-24 CH CH1221373A patent/CH581657A5/xx not_active IP Right Cessation
- 1973-08-24 CH CH796276A patent/CH581139A5/xx not_active IP Right Cessation
- 1973-08-27 BG BG025537A patent/BG21024A3/xx unknown
- 1973-08-27 BG BG024398A patent/BG19797A3/xx unknown
- 1973-08-27 HU HUBO1459A patent/HU166366B/hu unknown
- 1973-08-27 ES ES418271A patent/ES418271A1/es not_active Expired
- 1973-08-27 SU SU1962548A patent/SU485596A3/ru active
- 1973-08-27 CS CS7300005972A patent/CS179427B2/cs unknown
- 1973-08-27 SU SU1962550A patent/SU482042A3/ru active
- 1973-08-27 ZA ZA00735838A patent/ZA735838B/xx unknown
- 1973-08-28 IL IL43096A patent/IL43096A/en unknown
- 1973-08-28 JP JP48096558A patent/JPS4956999A/ja active Pending
- 1973-08-28 NL NL7311799A patent/NL7311799A/xx not_active Application Discontinuation
- 1973-08-28 GB GB4041773A patent/GB1439990A/en not_active Expired
- 1973-08-28 CA CA179,828A patent/CA1016951A/en not_active Expired
- 1973-08-28 US US392182A patent/US3901925A/en not_active Expired - Lifetime
- 1973-08-28 AU AU59708/73A patent/AU464515B2/en not_active Expired
- 1973-08-28 NO NO3383/73A patent/NO138567C/no unknown
- 1973-08-28 SE SE7311690A patent/SE396389B/xx unknown
- 1973-08-28 DE DE2343291A patent/DE2343291C3/de not_active Expired
- 1973-08-28 PL PL1973164886A patent/PL85433B1/pl unknown
- 1973-08-28 DK DK471873AA patent/DK131569B/da unknown
- 1973-08-28 BE BE135029A patent/BE804123A/xx unknown
- 1973-08-29 DD DD173155A patent/DD109870A5/xx unknown
- 1973-08-29 FR FR7331242A patent/FR2197594B1/fr not_active Expired
- 1973-08-29 IE IE1521/73A patent/IE38317B1/xx unknown
-
1975
- 1975-04-29 ES ES437148A patent/ES437148A1/es not_active Expired
-
1979
- 1979-06-21 IT IT7949487A patent/IT7949487A0/it unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL105962B1 (pl) | Sposob wytwarzania nowych pochodnych tieno/2,3-c/pirydyny | |
| US4110337A (en) | Triazolobenzodiazepines | |
| PL130691B1 (en) | Process for preparing novel heterocyclic compounds | |
| US3993656A (en) | 1,8-Naphthyridine compounds | |
| US4375479A (en) | Indanyl derivatives and use | |
| US3843663A (en) | 1,8-naphthyridine compounds | |
| JPS6037116B2 (ja) | ２―置換オキサゾロピリジン | |
| JPS61130284A (ja) | ハロゲノヒドロキシフラボン化合物 | |
| PL85433B1 (US20080293856A1-20081127-C00127.png) | ||
| JPS5829309B2 (ja) | コウアレルギ−セイサンカンシキカゴウブツノ セイゾウホウホウ | |
| EP0055068B1 (en) | Quinolone derivatives and their use as pharmaceuticals | |
| US4163785A (en) | Benzothiazepine compounds and compositions | |
| JPS5982367A (ja) | ６−置換キノリン−５，８−キノン類 | |
| US3946012A (en) | 6-L-dihydroxyethyl-2,4,7-trioxo-8-D-ribityl pteridine and process for producing the same | |
| US3842087A (en) | 1,8-naphthyridine compounds | |
| US3984534A (en) | Tetrazolyl anthraquinones for inhibiting the release of spasmogen mediators | |
| US3962262A (en) | 1,8-naphthyridine compounds | |
| US3984429A (en) | Pharmaceutically active compounds | |
| JPH0348906B2 (US20080293856A1-20081127-C00127.png) | ||
| US4031103A (en) | 1,8-Naphthyridine compounds | |
| US4302463A (en) | 1-Azaxanthone-3-carboxylic acids and their production | |
| JPS6324498B2 (US20080293856A1-20081127-C00127.png) | ||
| JPS6110587A (ja) | １−アザキサントン−３−カルボン酸誘導体およびその製造法 | |
| US2654753A (en) | 2-sulfanilamido-5-aminopyrimidine and salts thereof | |
| Freedman et al. | Arsenoso derivatives of phenyl-substituted fatty acids |
