DK166879B1 - Phenoxyeddikesyrederivater samt fremgangsmaader til fremstilling deraf og farmaceutiske praeparater indeholdende forbindelserne - Google Patents
Phenoxyeddikesyrederivater samt fremgangsmaader til fremstilling deraf og farmaceutiske praeparater indeholdende forbindelserne Download PDFInfo
- Publication number
- DK166879B1 DK166879B1 DK532987A DK532987A DK166879B1 DK 166879 B1 DK166879 B1 DK 166879B1 DK 532987 A DK532987 A DK 532987A DK 532987 A DK532987 A DK 532987A DK 166879 B1 DK166879 B1 DK 166879B1
- Authority
- DK
- Denmark
- Prior art keywords
- compound
- formula
- pyrazolyl
- dichloro
- salt
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 88
- 239000002253 acid Substances 0.000 title description 9
- 238000000034 method Methods 0.000 title description 2
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- -1 5-pyrazolyl group Chemical group 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 35
- 239000000460 chlorine Substances 0.000 claims description 16
- 238000001816 cooling Methods 0.000 claims description 5
- VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- ZXALCVLBUDYEFN-UHFFFAOYSA-N 2-[2,3-dichloro-4-(2-ethylpyrazole-3-carbonyl)phenoxy]acetic acid Chemical group CCN1N=CC=C1C(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl ZXALCVLBUDYEFN-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- ASXGXFSUUJHJFE-UHFFFAOYSA-N 2-[2,3-dichloro-4-[1-(2-methylpyrazol-3-yl)ethenyl]phenoxy]acetic acid Chemical group CN1N=CC=C1C(=C)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl ASXGXFSUUJHJFE-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000002934 diuretic Substances 0.000 abstract description 12
- 230000001882 diuretic effect Effects 0.000 abstract description 9
- 230000003424 uricosuric effect Effects 0.000 abstract description 7
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 230000000894 saliuretic effect Effects 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- 241000700159 Rattus Species 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical group N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 6
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
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- 238000012360 testing method Methods 0.000 description 6
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- 230000002485 urinary effect Effects 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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- 239000002585 base Substances 0.000 description 4
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- NBFHHTCEVGJOHQ-UHFFFAOYSA-N 2-[2,3-dichloro-4-[2-(ethoxymethyl)pyrazole-3-carbonyl]phenoxy]acetic acid Chemical compound CCOCN1N=CC=C1C(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl NBFHHTCEVGJOHQ-UHFFFAOYSA-N 0.000 description 3
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- CAXRIKJTCHLXAD-UHFFFAOYSA-N ethyl 2-[2,3-dichloro-4-[2-(ethoxymethyl)pyrazole-3-carbonyl]phenoxy]acetate Chemical compound CCOCN1N=CC=C1C(=O)C1=CC=C(OCC(=O)OCC)C(Cl)=C1Cl CAXRIKJTCHLXAD-UHFFFAOYSA-N 0.000 description 3
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- GEORDJYJYUGGSO-UHFFFAOYSA-N 2,3-dichloro-4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(Cl)=C1Cl GEORDJYJYUGGSO-UHFFFAOYSA-N 0.000 description 2
- UMGXHVUVCWTIDX-UHFFFAOYSA-N 2,3-dichloro-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(Cl)=C1Cl UMGXHVUVCWTIDX-UHFFFAOYSA-N 0.000 description 2
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- 241000521257 Hydrops Species 0.000 description 2
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- 201000001431 Hyperuricemia Diseases 0.000 description 1
- 206010027406 Mesothelioma Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010037423 Pulmonary oedema Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- PQFZWNNSXMOCAL-UHFFFAOYSA-N acetyl acetate;methylsulfinylmethane Chemical compound CS(C)=O.CC(=O)OC(C)=O PQFZWNNSXMOCAL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical compound OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 229960002155 chlorothiazide Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 1
- FASXZKDJUYYPLJ-UHFFFAOYSA-N ethyl 2-[2,3-dichloro-4-[[2-(ethoxymethyl)pyrazol-3-yl]-hydroxymethyl]phenoxy]acetate Chemical compound CCOCN1N=CC=C1C(O)C1=CC=C(OCC(=O)OCC)C(Cl)=C1Cl FASXZKDJUYYPLJ-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229960003883 furosemide Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- MOTRZVVGCFFABN-UHFFFAOYSA-N hexane;2-propan-2-yloxypropane Chemical compound CCCCCC.CC(C)OC(C)C MOTRZVVGCFFABN-UHFFFAOYSA-N 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000002171 loop diuretic Substances 0.000 description 1
- 208000002502 lymphedema Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- VYQLXFDWYFQLHL-UHFFFAOYSA-M potassium;2-thiophen-2-ylacetate Chemical compound [K+].[O-]C(=O)CC1=CC=CS1 VYQLXFDWYFQLHL-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 208000005333 pulmonary edema Diseases 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository 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
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 210000005239 tubule Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric 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
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24280286 | 1986-10-13 | ||
| JP24280286 | 1986-10-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK532987D0 DK532987D0 (da) | 1987-10-12 |
| DK532987A DK532987A (da) | 1988-04-14 |
| DK166879B1 true DK166879B1 (da) | 1993-07-26 |
Family
ID=17094503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK532987A DK166879B1 (da) | 1986-10-13 | 1987-10-12 | Phenoxyeddikesyrederivater samt fremgangsmaader til fremstilling deraf og farmaceutiske praeparater indeholdende forbindelserne |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4853404A (https=) |
| EP (1) | EP0268800B1 (https=) |
| JP (1) | JPS63225359A (https=) |
| KR (1) | KR920002296B1 (https=) |
| CN (1) | CN1014787B (https=) |
| AT (1) | ATE72429T1 (https=) |
| AU (1) | AU595385B2 (https=) |
| CA (1) | CA1311483C (https=) |
| DE (1) | DE3776627D1 (https=) |
| DK (1) | DK166879B1 (https=) |
| ES (1) | ES2032284T3 (https=) |
| FI (1) | FI91402C (https=) |
| GR (1) | GR3003727T3 (https=) |
| HK (1) | HK47193A (https=) |
| HU (1) | HU202501B (https=) |
| IE (1) | IE60044B1 (https=) |
| IL (1) | IL84106A (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2613720B1 (fr) * | 1987-04-10 | 1990-01-19 | Esteve Labor Dr | Derives d'aryl-heteroaryl carbinols avec activite analgesique |
| JPH01316317A (ja) * | 1988-03-10 | 1989-12-21 | Tanabe Seiyaku Co Ltd | 降圧剤 |
| US4956379A (en) * | 1990-02-13 | 1990-09-11 | Bristol-Myers Squibb Company | Pyrazole carboxylic acids and esters and inhibition of blood platelet aggregation therewith |
| EP0442448A3 (en) | 1990-02-13 | 1992-08-12 | Bristol-Myers Squibb Company | Heterocyclic carboxylic acids and esters |
| US20040067531A1 (en) * | 1997-08-20 | 2004-04-08 | Sugen, Inc. | Methods of modulating protein tyrosine kinase function with substituted indolinone compounds |
| SI1255752T1 (sl) * | 2000-02-15 | 2007-12-31 | Pharmacia & Upjohn Co Llc | S pirolom substituirani zaviralci 2-indolinon protein kinaza |
| AR042586A1 (es) | 2001-02-15 | 2005-06-29 | Sugen Inc | 3-(4-amidopirrol-2-ilmetiliden)-2-indolinona como inhibidores de la protein quinasa; sus composiciones farmaceuticas; un metodo para la modulacion de la actividad catalitica de la proteinquinasa; un metodo para tratar o prevenir una afeccion relacionada con la proteinquinasa |
| WO2003031438A1 (en) | 2001-10-10 | 2003-04-17 | Sugen, Inc. | 3-[4-(substituted heterocyclyl)-pyrrol-2-ylmethylidene]-2-indolinone derivatives as kinase inhibitors |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3342851A (en) * | 1964-10-30 | 1967-09-19 | Merck & Co Inc | Esters of [(2-methyleneacyl)phenoxy]-carboxylic acids and a method for their preparation |
| GB1415295A (en) * | 1971-10-14 | 1975-11-26 | Orchimed Sa | Substituted phenoxy-alkyl-carboxylic acids and derivatives thereof |
| CH543472A (fr) * | 1969-01-31 | 1973-10-31 | Orchimed Sa | Procédé pour la préparation d'acides phénoxyalcoyl-carboxyliques |
| US4107179A (en) * | 1977-08-22 | 1978-08-15 | Smithkline Corporation | Method for preparing ticrynafen |
| GB2024209B (en) * | 1978-05-31 | 1982-09-08 | Sori Soc Rech Ind | Phenoxalkylcarboxylic acids |
| US4323691A (en) * | 1979-10-09 | 1982-04-06 | Abbott Laboratories | Hydroxyaminomethyl derivatives of benzoyl di-substituted α-phenoxyalkanoyl esters |
-
1987
- 1987-10-05 US US07/105,173 patent/US4853404A/en not_active Expired - Fee Related
- 1987-10-06 IL IL84106A patent/IL84106A/xx not_active IP Right Cessation
- 1987-10-06 IE IE266887A patent/IE60044B1/en not_active IP Right Cessation
- 1987-10-09 JP JP62255347A patent/JPS63225359A/ja active Granted
- 1987-10-10 CN CN87106895A patent/CN1014787B/zh not_active Expired
- 1987-10-12 KR KR1019870011259A patent/KR920002296B1/ko not_active Expired
- 1987-10-12 DK DK532987A patent/DK166879B1/da active
- 1987-10-12 DE DE8787114877T patent/DE3776627D1/de not_active Expired - Lifetime
- 1987-10-12 AT AT87114877T patent/ATE72429T1/de not_active IP Right Cessation
- 1987-10-12 HU HU874600A patent/HU202501B/hu not_active IP Right Cessation
- 1987-10-12 ES ES198787114877T patent/ES2032284T3/es not_active Expired - Lifetime
- 1987-10-12 EP EP87114877A patent/EP0268800B1/en not_active Expired - Lifetime
- 1987-10-12 AU AU79563/87A patent/AU595385B2/en not_active Ceased
- 1987-10-12 FI FI874473A patent/FI91402C/fi not_active IP Right Cessation
- 1987-10-13 CA CA000549137A patent/CA1311483C/en not_active Expired - Lifetime
-
1992
- 1992-02-06 GR GR910401089T patent/GR3003727T3/el unknown
-
1993
- 1993-05-13 HK HK471/93A patent/HK47193A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR3003727T3 (https=) | 1993-03-16 |
| EP0268800A1 (en) | 1988-06-01 |
| US4853404A (en) | 1989-08-01 |
| CN1014787B (zh) | 1991-11-20 |
| KR880005089A (ko) | 1988-06-28 |
| KR920002296B1 (ko) | 1992-03-21 |
| AU595385B2 (en) | 1990-03-29 |
| JPH0544944B2 (https=) | 1993-07-07 |
| CA1311483C (en) | 1992-12-15 |
| ES2032284T3 (es) | 1993-02-01 |
| FI91402B (fi) | 1994-03-15 |
| CN87106895A (zh) | 1988-04-20 |
| HK47193A (en) | 1993-05-21 |
| FI874473A0 (fi) | 1987-10-12 |
| AU7956387A (en) | 1988-04-14 |
| JPS63225359A (ja) | 1988-09-20 |
| DK532987D0 (da) | 1987-10-12 |
| DK532987A (da) | 1988-04-14 |
| FI91402C (fi) | 1994-06-27 |
| DE3776627D1 (de) | 1992-03-19 |
| EP0268800B1 (en) | 1992-02-05 |
| IE60044B1 (en) | 1994-05-18 |
| IE872668L (en) | 1988-04-13 |
| ATE72429T1 (de) | 1992-02-15 |
| HU202501B (en) | 1991-03-28 |
| IL84106A0 (en) | 1988-03-31 |
| IL84106A (en) | 1991-07-18 |
| FI874473L (fi) | 1988-04-14 |
| HUT50788A (en) | 1990-03-28 |
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