PH26567A - Process and intermediates for the preparation of oxophthalazinyl acetic acids and analogs thereof - Google Patents

Process and intermediates for the preparation of oxophthalazinyl acetic acids and analogs thereof Download PDF

Info

Publication number: PH26567A
Authority: PH; Philippines
Prior art keywords: compound; oxo; formula; solution; alkyl
Prior art date: 1989-05-11

Application number

PH40512A

Other languages

English (en)

Inventor

Banavara Lakshmana Mylari

William James Zembrowski

Original Assignee

Pfizer

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.)

1989-05-11

Filing date

1990-05-11

Publication date

1992-08-19

1990-05-11 Application filed by Pfizer filed Critical Pfizer

1992-08-19 Publication of PH26567A publication Critical patent/PH26567A/en

Links

238000000034 method Methods 0.000 title description 9
235000011054 acetic acid Nutrition 0.000 title description 6
238000002360 preparation method Methods 0.000 title description 5
239000000543 intermediate Substances 0.000 title description 3
150000001243 acetic acids Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 38
125000000217 alkyl group Chemical group 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000001246 bromo group Chemical group Br* 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
125000005530 alkylenedioxy group Chemical group 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 9
229910000037 hydrogen sulfide Inorganic materials 0.000 description 9
239000007787 solid Substances 0.000 description 9
-1 2-substituted aniline Chemical class 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
241000700159 Rattus Species 0.000 description 6
239000000047 product Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000005457 ice water Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 5
150000003512 tertiary amines Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
102000016912 Aldehyde Reductase Human genes 0.000 description 4
108010053754 Aldehyde reductase Proteins 0.000 description 4
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000001684 chronic effect Effects 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
206010012601 diabetes mellitus Diseases 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
238000010992 reflux Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000000600 sorbitol Substances 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
TZGFQIXRVUHDLE-UHFFFAOYSA-N 1-chloro-2-nitro-4-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1Cl TZGFQIXRVUHDLE-UHFFFAOYSA-N 0.000 description 3
RIIVBOIBIOLLPO-UHFFFAOYSA-N 2-phthalazin-1-ylacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=NN=CC2=C1 RIIVBOIBIOLLPO-UHFFFAOYSA-N 0.000 description 3
208000002177 Cataract Diseases 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
206010007749 Cataract diabetic Diseases 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
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 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
238000009825 accumulation Methods 0.000 description 2
239000003288 aldose reductase inhibitor Substances 0.000 description 2
229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
201000007025 diabetic cataract Diseases 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000008103 glucose Substances 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000010410 layer Substances 0.000 description 2
GJIMTGCSEXYRCB-UHFFFAOYSA-N methyl 2-(2h-indazol-3-yl)acetate Chemical compound C1=CC=C2C(CC(=O)OC)=NNC2=C1 GJIMTGCSEXYRCB-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
210000003497 sciatic nerve Anatomy 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
JEEDFPVACIKHEU-UHFFFAOYSA-N 2-(2h-indazol-3-yl)acetic acid Chemical compound C1=CC=CC2=C(CC(=O)O)NN=C21 JEEDFPVACIKHEU-UHFFFAOYSA-N 0.000 description 1
VMVSSVCXGNALAH-UHFFFAOYSA-N 2-(chloromethyl)-5-(trifluoromethyl)-1,3-benzothiazole Chemical compound FC(F)(F)C1=CC=C2SC(CCl)=NC2=C1 VMVSSVCXGNALAH-UHFFFAOYSA-N 0.000 description 1
XAOWOQZGDIZZDA-UHFFFAOYSA-N 3,6-dichloro-1-fluoro-6-nitrocyclohexa-1,3-diene Chemical compound ClC1(CC=C(C=C1F)Cl)[N+](=O)[O-] XAOWOQZGDIZZDA-UHFFFAOYSA-N 0.000 description 1
WTFUTSCZYYCBAY-SXBRIOAWSA-N 6-[(E)-C-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-N-hydroxycarbonimidoyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C/C(=N/O)/C1=CC2=C(NC(O2)=O)C=C1 WTFUTSCZYYCBAY-SXBRIOAWSA-N 0.000 description 1
101001053401 Arabidopsis thaliana Acid beta-fructofuranosidase 3, vacuolar Proteins 0.000 description 1
101001028732 Chironex fleckeri Toxin CfTX-A Proteins 0.000 description 1
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
208000002249 Diabetes Complications Diseases 0.000 description 1
206010012655 Diabetic complications Diseases 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
208000017442 Retinal disease Diseases 0.000 description 1
206010038923 Retinopathy Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 1
ZWZUFQPXYVYAFO-UHFFFAOYSA-N Tert-butyl (triphenylphosphoranylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC(C)(C)C)C1=CC=CC=C1 ZWZUFQPXYVYAFO-UHFFFAOYSA-N 0.000 description 1
125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 1
239000002253 acid Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004799 bromophenyl group Chemical group 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000010908 decantation Methods 0.000 description 1
FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
MCQOWYALZVKMAR-UHFFFAOYSA-N furo[3,4-b]pyridine-5,7-dione Chemical compound C1=CC=C2C(=O)OC(=O)C2=N1 MCQOWYALZVKMAR-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
208000017169 kidney disease Diseases 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
201000001119 neuropathy Diseases 0.000 description 1
230000007823 neuropathy Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Substances [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
229960001052 streptozocin Drugs 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

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Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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PH40512A 1989-05-11 1990-05-11 Process and intermediates for the preparation of oxophthalazinyl acetic acids and analogs thereof PH26567A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/350,997 US4954629A (en)	1989-05-11	1989-05-11	Process and intermediates for the preparation of oxophthalazinyl acetic acids and analogs thereof

Publications (1)

Publication Number	Publication Date
PH26567A true PH26567A (en)	1992-08-19

Family

ID=23379152

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH40512A PH26567A (en)	1989-05-11	1990-05-11	Process and intermediates for the preparation of oxophthalazinyl acetic acids and analogs thereof

Country Status (30)

Country	Link
US (1)	US4954629A (sh)
EP (1)	EP0397350B1 (sh)
JP (1)	JPH035479A (sh)
KR (1)	KR920006419B1 (sh)
CN (1)	CN1025855C (sh)
AR (1)	AR246968A1 (sh)
AT (1)	ATE103913T1 (sh)
AU (2)	AU618898B2 (sh)
BG (1)	BG50609A3 (sh)
CA (1)	CA2016504C (sh)
CZ (1)	CZ281213B6 (sh)
DD (1)	DD294257A5 (sh)
DE (1)	DE69007846T2 (sh)
DK (1)	DK0397350T3 (sh)
EG (1)	EG19082A (sh)
ES (1)	ES2063265T3 (sh)
FI (1)	FI93959C (sh)
HU (1)	HU212304B (sh)
IE (1)	IE62591B1 (sh)
IL (3)	IL114271A (sh)
MX (2)	MX167455B (sh)
NO (1)	NO177708C (sh)
NZ (1)	NZ233597A (sh)
PH (1)	PH26567A (sh)
PL (1)	PL164427B1 (sh)
PT (1)	PT93985B (sh)
RO (1)	RO107256B1 (sh)
RU (1)	RU2014333C1 (sh)
YU (1)	YU91290A (sh)
ZA (1)	ZA903565B (sh)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4996204A (en) *	1989-05-11	1991-02-26	Pfizer Inc.	Pyrido[2,3-d]pyridazinones as aldose reductase inhibitors
IL124236A (en) *	1997-05-05	2003-01-12	Pfizer	Pharmaceutical composition for treating or reversing diabetic cardiomyopathy comprising aldose reductase inhibitor
EP0982306A3 (en) *	1998-08-21	2000-07-05	Pfizer Products Inc.	Polymorph of zopolrestat monohydrate
CN105732640B (zh)	2010-07-16	2019-01-08	纽约市哥伦比亚大学理事会	醛糖还原酶抑制剂及其用途
US8916563B2 (en)	2010-07-16	2014-12-23	The Trustees Of Columbia University In The City Of New York	Aldose reductase inhibitors and uses thereof
CN102558184B (zh) *	2011-12-30	2014-07-16	西南大学	酞嗪类衍生物的合成方法
CN102702108A (zh) *	2012-06-27	2012-10-03	上海大学	1,2-二氢酞嗪类化合物及其合成方法
CN102863393A (zh) *	2012-09-26	2013-01-09	上海大学	1,2-二氢酞嗪类化合物及其合成方法
SI3352754T1 (sl)	2016-06-21	2021-03-31	The Trustees Of Columbia University In The City Of New York	Zaviralci aldozne reduktaze in postopki njihove uporabe
PL3658142T3 (pl)	2017-07-28	2024-08-26	Applied Therapeutics, Inc.	Związki i sposoby leczenia galaktozemii
CA3132136A1 (en)	2019-04-01	2020-10-08	Andrew Wasmuth	Inhibitors of aldose reductase
CN113966396A (zh)	2019-05-07	2022-01-21	迈阿密大学	遗传性神经病和相关障碍的治疗和检测

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE47592B1 (en) *	1977-12-29	1984-05-02	Ici Ltd	Enzyme inhibitory phthalazin-4-ylacetic acid derivatives, pharmaceutical compositions thereof,and process for their manufacture
DE3337859A1 (de) *	1983-01-21	1984-07-26	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von benzthiazolen
EP0222576B1 (en) *	1985-11-07	1992-03-18	Pfizer Inc.	Heterocyclic oxophthalazinyl acetic acids
CA1299178C (en) *	1985-11-07	1992-04-21	Banavara Lakshmana Mylari	Heterocyclic oxophtalazinyl acetic acids
JPH0676391B2 (ja) *	1987-06-09	1994-09-28	フアイザー・インコーポレイテツド	ベンゾチアゾール等の複素環側鎖を有するオキソフタラジニル酢酸類の製造方法
EP0322153A3 (en) *	1987-12-21	1990-08-16	Pfizer Inc.	Heterocyclic oxophtalazinyl acetic acids
WO1989006651A1 (en) *	1988-01-19	1989-07-27	Pfizer Inc.	1h-indazole-3-acetic acids as aldose reductase inhibitors
US4996204A (en) *	1989-05-11	1991-02-26	Pfizer Inc.	Pyrido[2,3-d]pyridazinones as aldose reductase inhibitors

1989
- 1989-05-11 US US07/350,997 patent/US4954629A/en not_active Expired - Lifetime
1990
- 1990-04-25 AT AT90304441T patent/ATE103913T1/de not_active IP Right Cessation
- 1990-04-25 DE DE69007846T patent/DE69007846T2/de not_active Expired - Fee Related
- 1990-04-25 DK DK90304441.0T patent/DK0397350T3/da active
- 1990-04-25 ES ES90304441T patent/ES2063265T3/es not_active Expired - Lifetime
- 1990-04-25 EP EP90304441A patent/EP0397350B1/en not_active Expired - Lifetime
- 1990-05-02 RO RO144965A patent/RO107256B1/ro unknown
- 1990-05-04 IE IE162690A patent/IE62591B1/en not_active IP Right Cessation
- 1990-05-06 IL IL114271A patent/IL114271A/en not_active IP Right Cessation
- 1990-05-06 IL IL9430190A patent/IL94301A/en not_active IP Right Cessation
- 1990-05-08 CZ CS902278A patent/CZ281213B6/cs not_active IP Right Cessation
- 1990-05-08 NZ NZ233597A patent/NZ233597A/en unknown
- 1990-05-09 PT PT93985A patent/PT93985B/pt not_active IP Right Cessation
- 1990-05-09 PL PL90285113A patent/PL164427B1/pl unknown
- 1990-05-10 ZA ZA903565A patent/ZA903565B/xx unknown
- 1990-05-10 AU AU54906/90A patent/AU618898B2/en not_active Ceased
- 1990-05-10 CA CA002016504A patent/CA2016504C/en not_active Expired - Fee Related
- 1990-05-10 DD DD90340590A patent/DD294257A5/de not_active IP Right Cessation
- 1990-05-10 HU HU902995A patent/HU212304B/hu not_active IP Right Cessation
- 1990-05-10 EG EG27690A patent/EG19082A/xx active
- 1990-05-10 CN CN90102797A patent/CN1025855C/zh not_active Expired - Fee Related
- 1990-05-10 BG BG091982A patent/BG50609A3/xx unknown
- 1990-05-10 RU SU904743977A patent/RU2014333C1/ru active
- 1990-05-10 FI FI902333A patent/FI93959C/fi not_active IP Right Cessation
- 1990-05-10 AR AR90316824A patent/AR246968A1/es active
- 1990-05-10 YU YU91290A patent/YU91290A/sh unknown
- 1990-05-10 KR KR1019900006579A patent/KR920006419B1/ko not_active IP Right Cessation
- 1990-05-10 NO NO902071A patent/NO177708C/no not_active IP Right Cessation
- 1990-05-11 MX MX020672A patent/MX167455B/es unknown
- 1990-05-11 PH PH40512A patent/PH26567A/en unknown
- 1990-05-11 JP JP2122862A patent/JPH035479A/ja active Granted
1991
- 1991-10-28 AU AU86806/91A patent/AU626225B2/en not_active Ceased
1992
- 1992-12-31 MX MX9207687A patent/MX9207687A/es not_active IP Right Cessation
1995
- 1995-06-22 IL IL11427195A patent/IL114271A0/xx unknown

Also Published As

Publication number	Publication date
RU2014333C1 (ru)	1994-06-15
IL114271A0 (en)	1995-10-31
FI93959B (fi)	1995-03-15
CA2016504C (en)	1999-07-27
PT93985A (pt)	1991-01-08
EP0397350A1 (en)	1990-11-14
IL94301A0 (en)	1991-03-10
US4954629A (en)	1990-09-04
CN1047499A (zh)	1990-12-05
HUT54690A (en)	1991-03-28
IL94301A (en)	1996-01-19
IL114271A (en)	1998-04-05
KR900018114A (ko)	1990-12-20
BG50609A3 (en)	1992-09-15
CA2016504A1 (en)	1990-11-11
AU626225B2 (en)	1992-07-23
CZ281213B6 (cs)	1996-07-17
AU5490690A (en)	1990-11-15
IE62591B1 (en)	1995-02-08
NO902071D0 (no)	1990-05-10
RO107256B1 (ro)	1993-10-30
MX167455B (es)	1993-03-23
ZA903565B (en)	1991-12-24
FI902333A0 (fi)	1990-05-10
FI93959C (fi)	1995-06-26
ES2063265T3 (es)	1995-01-01
PL285113A1 (en)	1991-07-15
KR920006419B1 (ko)	1992-08-06
AU618898B2 (en)	1992-01-09
NO177708C (no)	1995-11-08
NZ233597A (en)	1992-02-25
DE69007846T2 (de)	1994-07-28
NO902071L (no)	1990-11-12
ATE103913T1 (de)	1994-04-15
YU91290A (sh)	1992-09-07
CZ227890A3 (en)	1996-04-17
PT93985B (pt)	1996-11-29
IE901626L (en)	1990-11-11
DD294257A5 (de)	1991-09-26
EG19082A (en)	1994-07-30
AU8680691A (en)	1992-01-02
HU902995D0 (en)	1990-09-28
JPH035479A (ja)	1991-01-11
DE69007846D1 (de)	1994-05-11
CN1025855C (zh)	1994-09-07
EP0397350B1 (en)	1994-04-06
NO177708B (no)	1995-07-31
MX9207687A (es)	1994-06-30
AR246968A1 (es)	1994-10-31
HU212304B (en)	1996-05-28
JPH0573753B2 (sh)	1993-10-15
DK0397350T3 (da)	1994-05-09
PL164427B1 (pl)	1994-07-29

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US5304557A (en)	1994-04-19	Substituted oxoophthalazinyl acetic acids and analogs thereof
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WO2008077305A1 (fr)	2008-07-03	Composés de quinoléine, intermédiaires, procédés de préparation et utilisations de ceux-ci
US5171862A (en)	1992-12-15	Process and indazole intermediates for the preparation of oxophthalazinyl acetic acids and analogs thereof
US5182391A (en)	1993-01-26	Process and intermediates for the preparation of oxophthalazinyl acetic acids and analogs thereof
US5075442A (en)	1991-12-24	Process and intermediates for the preparation of oxophthalazinyl acetic acids and analogs thereof
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HU185318B (en)	1985-01-28	Process for preparing pyrimid 0/6,1-a/ isoquinolin-4-one derivatives
JPH06135959A (ja)	1994-05-17	カルボスチリル誘導体