AU2002319693B2 - Indane acetic acid derivatives and their use as pharmaceutical agents, intermediates, and method of preparation - Google Patents
Indane acetic acid derivatives and their use as pharmaceutical agents, intermediates, and method of preparation Download PDFInfo
- Publication number
- AU2002319693B2 AU2002319693B2 AU2002319693A AU2002319693A AU2002319693B2 AU 2002319693 B2 AU2002319693 B2 AU 2002319693B2 AU 2002319693 A AU2002319693 A AU 2002319693A AU 2002319693 A AU2002319693 A AU 2002319693A AU 2002319693 B2 AU2002319693 B2 AU 2002319693B2
- Authority
- AU
- Australia
- Prior art keywords
- substituted
- inden
- methyl
- phenyl
- unsubstituted
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 238000000034 method Methods 0.000 title claims description 126
- 238000002360 preparation method Methods 0.000 title claims description 87
- BUVKILSTJGGJJN-UHFFFAOYSA-N acetic acid;2,3-dihydro-1h-indene Chemical class CC(O)=O.C1=CC=C2CCCC2=C1 BUVKILSTJGGJJN-UHFFFAOYSA-N 0.000 title description 5
- 239000008177 pharmaceutical agent Substances 0.000 title description 3
- 239000012450 pharmaceutical intermediate Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 224
- -1 methylenedioxyphenyl Chemical group 0.000 claims description 218
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 205
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 139
- 239000000203 mixture Substances 0.000 claims description 102
- 239000002253 acid Substances 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- 125000001153 fluoro group Chemical group F* 0.000 claims description 82
- 125000001544 thienyl group Chemical group 0.000 claims description 70
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 69
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 68
- 150000003839 salts Chemical class 0.000 claims description 68
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 67
- 125000002757 morpholinyl group Chemical group 0.000 claims description 67
- 125000004193 piperazinyl group Chemical group 0.000 claims description 67
- 125000004076 pyridyl group Chemical group 0.000 claims description 67
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 67
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 67
- 125000000335 thiazolyl group Chemical group 0.000 claims description 67
- 125000001425 triazolyl group Chemical group 0.000 claims description 67
- 125000002971 oxazolyl group Chemical group 0.000 claims description 66
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 66
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 65
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 65
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 65
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 63
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 63
- 125000003386 piperidinyl group Chemical group 0.000 claims description 62
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 62
- 125000002541 furyl group Chemical group 0.000 claims description 60
- 239000002904 solvent Substances 0.000 claims description 59
- 125000002883 imidazolyl group Chemical group 0.000 claims description 58
- 125000003545 alkoxy group Chemical group 0.000 claims description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- 229910052740 iodine Inorganic materials 0.000 claims description 51
- 125000005843 halogen group Chemical group 0.000 claims description 50
- 125000001041 indolyl group Chemical group 0.000 claims description 50
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 125000004043 oxo group Chemical group O=* 0.000 claims description 46
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 45
- 230000008569 process Effects 0.000 claims description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- 150000002148 esters Chemical class 0.000 claims description 39
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 38
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 38
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 38
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 38
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 38
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 38
- 125000001624 naphthyl group Chemical group 0.000 claims description 38
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 38
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 38
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 38
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 38
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 37
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 37
- 125000004586 dihydrobenzopyranyl group Chemical group O1C(CCC2=C1C=CC=C2)* 0.000 claims description 37
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 37
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 37
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 37
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 36
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 36
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 125000005493 quinolyl group Chemical group 0.000 claims description 36
- 125000004597 dihydrobenzothiopyranyl group Chemical group S1C(CCC2=C1C=CC=C2)* 0.000 claims description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 34
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims description 25
- 238000005984 hydrogenation reaction Methods 0.000 claims description 25
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 23
- 206010012601 diabetes mellitus Diseases 0.000 claims description 22
- 238000002425 crystallisation Methods 0.000 claims description 21
- 230000008025 crystallization Effects 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 20
- 102000004877 Insulin Human genes 0.000 claims description 19
- 108090001061 Insulin Proteins 0.000 claims description 19
- 229940125396 insulin Drugs 0.000 claims description 19
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 239000003472 antidiabetic agent Substances 0.000 claims description 18
- 229940126904 hypoglycaemic agent Drugs 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 15
- 206010022489 Insulin Resistance Diseases 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- 206010020772 Hypertension Diseases 0.000 claims description 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 10
- 208000029078 coronary artery disease Diseases 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 230000009467 reduction Effects 0.000 claims description 10
- 208000011580 syndromic disease Diseases 0.000 claims description 10
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 9
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 9
- 239000011707 mineral Substances 0.000 claims description 9
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 235000019260 propionic acid Nutrition 0.000 claims description 9
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 8
- 201000008980 hyperinsulinism Diseases 0.000 claims description 8
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 7
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 7
- 208000008589 Obesity Diseases 0.000 claims description 7
- 230000003143 atherosclerotic effect Effects 0.000 claims description 7
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 6
- 206010056997 Impaired fasting glucose Diseases 0.000 claims description 6
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 6
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims description 5
- 235000001258 Cinchona calisaya Nutrition 0.000 claims description 5
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 230000037396 body weight Effects 0.000 claims description 5
- 229940125753 fibrate Drugs 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 5
- 201000001421 hyperglycemia Diseases 0.000 claims description 5
- 229960000948 quinine Drugs 0.000 claims description 5
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 208000005623 Carcinogenesis Diseases 0.000 claims description 4
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- 230000036952 cancer formation Effects 0.000 claims description 4
- 231100000504 carcinogenesis Toxicity 0.000 claims description 4
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 claims description 4
- KMPWYEUPVWOPIM-LSOMNZGLSA-N cinchonine Chemical compound C1=CC=C2C([C@@H]([C@H]3N4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-LSOMNZGLSA-N 0.000 claims description 4
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- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 3
- 229940122199 Insulin secretagogue Drugs 0.000 claims description 3
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- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 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 claims description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011995 wilkinson's catalyst Substances 0.000 claims description 3
- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 claims description 3
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- 229910052741 iridium Inorganic materials 0.000 claims description 2
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- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 9
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims 1
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- XBTMXQIEPLXCFE-UHFFFAOYSA-N 2-[5-[2-(2-cyclopentyl-5-methyl-1,3-oxazol-4-yl)ethoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound N=1C(CCOC=2C=C3CCC(CC(O)=O)C3=CC=2)=C(C)OC=1C1CCCC1 XBTMXQIEPLXCFE-UHFFFAOYSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
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| EP1578715B1 (en) | 2002-12-20 | 2011-03-02 | Bayer Pharmaceuticals Corporation | Indane acetic acid derivatives and their use as pharmaceutical agents, intermediates, and method of preparation |
| US7244763B2 (en) * | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
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| PL1954684T3 (pl) * | 2005-11-15 | 2014-10-31 | Otsuka Pharma Co Ltd | Związek oksazolowy i kompozycja farmaceutyczna |
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| US8633252B2 (en) * | 2009-01-26 | 2014-01-21 | Taipei Medical University | Use of pterosin compounds for treating diabetes and obesity |
| AR075401A1 (es) * | 2009-02-13 | 2011-03-30 | Sanofi Aventis | Indanos sustituidos, procesos para su preparacion y uso de los mismos como un medicamento |
| WO2010141690A2 (en) * | 2009-06-04 | 2010-12-09 | Dara Biosciences, Inc. | Indane analogs and use as pharmaceutical agents and process of making |
| US20180200230A1 (en) * | 2009-06-04 | 2018-07-19 | Dara Biosciences, Inc. | Methods of treating neurodegenerative diseases using indane acetic acid derivatives which penetrate the blood brain barrier |
| WO2010141696A1 (en) * | 2009-06-04 | 2010-12-09 | Dara Biosciences, Inc. | Methods of treating or preventing psoriasis, and/or alzheimer's disease using indane acetic acid derivatives |
| EP2473515A4 (en) | 2009-09-04 | 2013-11-27 | Univ Toledo | PROCESS FOR PREPARING OPTICALLY PURE BETA LACTONS FROM ALDEHYDE AND COMPOSITIONS MADE THEREOF |
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| CA2980296A1 (en) * | 2015-03-26 | 2016-09-29 | T3D Therapeutics, Inc. | Methods of treating liver disease using indane acetic acid derivatives |
| TWI712582B (zh) * | 2015-10-14 | 2020-12-11 | 法商領先藥物公司 | 用來製備(5s,10s)-10-苄基-16-甲基-11,14,18-三側氧基-15,17,19-三氧雜-2,7,8-三噻基-12-氮二十一烷基-5-銨基(e)-3-羧基丙烯酸鹽的工業方法 |
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| US10919852B2 (en) | 2017-07-28 | 2021-02-16 | Chemocentryx, Inc. | Immunomodulator compounds |
| CA3113689A1 (en) | 2018-09-25 | 2020-04-02 | Antabio Sas | Indane derivatives for use in the treatment of bacterial infection |
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| US3929923A (en) * | 1972-01-17 | 1975-12-30 | Sun Research Development | Process for preparation of isomers of 1-cyclohexyl-1,3,3-trimethylhydrindane |
| US4754043A (en) * | 1985-10-03 | 1988-06-28 | American Home Products Corporation | Oxazole and thiazole naphthalenes as antiallergic agents |
| FR2670491B1 (fr) * | 1990-12-14 | 1993-02-05 | Adir | Nouvelles piperazines 1,4-disubstituees, leur procede de preparation et les compositions pharmaceutiques les renfermant. |
| US5480896A (en) | 1994-01-27 | 1996-01-02 | American Home Products Corporation | Aralkyl-1,2,4-oxadiazolidine-3,5-diones as antihyperglycemic agents |
| US5939442A (en) | 1995-06-07 | 1999-08-17 | The Salk Institute For Biological Studies | Modulations of peroxisome proliferator activated receptor-γ, and methods for the use thereof |
| JPH1087602A (ja) * | 1996-09-09 | 1998-04-07 | Zeria Pharmaceut Co Ltd | スルホンアミド誘導体、それを含有するトロンボキサン拮抗剤及び該化合物の製造中間体 |
| WO1999011255A1 (en) * | 1997-08-28 | 1999-03-11 | Ono Pharmaceutical Co., Ltd. | Peroxisome proliferator-activated receptor controllers |
| PL351470A1 (en) | 1999-04-28 | 2003-04-22 | Aventis Pharma Gmbh | Tri-aryl acid derivatives as ppar receptor ligands |
| YU72201A (sh) | 1999-04-28 | 2005-07-19 | Aventis Pharma Deutschland Gmbh. | Derivati di-aril kiseline kao ppar receptorski ligandi |
| US6417212B1 (en) * | 1999-08-27 | 2002-07-09 | Eli Lilly & Company | Modulators of peroxisome proliferator activated receptors |
| JP2004509084A (ja) | 2000-08-23 | 2004-03-25 | イーライ・リリー・アンド・カンパニー | オキサゾリル−アリールオキシ酢酸誘導体およびそのpparアゴニストとしての使用 |
| AR036237A1 (es) * | 2001-07-27 | 2004-08-25 | Bayer Corp | Derivados del acido indan acetico, intermediarios, y metodo para su preparacion, composicion farmaceutica y el uso de dichos derivados para la manufactura de un medicamento |
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| NB | Applications allowed - extensions of time section 223(2) |
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