CA2126400A1 - Hypoglycemic agents - Google Patents
Hypoglycemic agentsInfo
- Publication number
- CA2126400A1 CA2126400A1 CA002126400A CA2126400A CA2126400A1 CA 2126400 A1 CA2126400 A1 CA 2126400A1 CA 002126400 A CA002126400 A CA 002126400A CA 2126400 A CA2126400 A CA 2126400A CA 2126400 A1 CA2126400 A1 CA 2126400A1
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- compound
- pharmaceutically acceptable
- hydroxy
- alkoxy
- 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.)
- Abandoned
Links
- 239000003472 antidiabetic agent Substances 0.000 title description 4
- 229940126904 hypoglycaemic agent Drugs 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 230000001833 anti-estrogenic effect Effects 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 239000000328 estrogen antagonist Substances 0.000 claims abstract description 33
- 229940046836 anti-estrogen Drugs 0.000 claims abstract description 30
- 239000012453 solvate Substances 0.000 claims abstract description 26
- -1 N-piperidinyl Chemical group 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 150000002431 hydrogen Chemical group 0.000 claims description 18
- 210000004369 blood Anatomy 0.000 claims description 16
- 239000008280 blood Substances 0.000 claims description 16
- 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 claims description 15
- 125000004423 acyloxy group Chemical group 0.000 claims description 14
- 239000008103 glucose Substances 0.000 claims description 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002757 morpholinyl group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 125000005333 aroyloxy group Chemical group 0.000 claims description 7
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical group C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 229910019142 PO4 Chemical group 0.000 claims description 3
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Chemical group 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- JLERVPBPJHKRBJ-UHFFFAOYSA-N LY 117018 Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCC3)=CC=2)C2=CC=C(O)C=C2S1 JLERVPBPJHKRBJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001907 coumarones Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 32
- 201000001421 hyperglycemia Diseases 0.000 abstract description 5
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 7
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- A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
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- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Medicines Containing Plant Substances (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyrane Compounds (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Thiazole And Isothizaole Compounds (AREA)
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| NO (1) | NO312398B1 (enExample) |
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| PH (1) | PH30490A (enExample) |
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| UA (1) | UA34441C2 (enExample) |
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| US6515009B1 (en) | 1991-09-27 | 2003-02-04 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
| US5811447A (en) | 1993-01-28 | 1998-09-22 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
| USRE39049E1 (en) | 1992-07-28 | 2006-03-28 | Eli Lilly And Company | Methods for inhibiting bone loss |
| USRE38968E1 (en) | 1992-07-28 | 2006-02-07 | Eli Lilly And Company | Methods for inhibiting bone loss using 6-hydroxy-2-(4-hydroxyphenyl)-benzo[b]thien-3-yl-4-[2-(piperidin-1-yl) ethoxyphenylimethanone hydrochloride |
| TW366342B (en) * | 1992-07-28 | 1999-08-11 | Lilly Co Eli | The use of 2-phenyl-3-aroylbenzothiophenes in inhibiting bone loss |
| US6251920B1 (en) | 1993-05-13 | 2001-06-26 | Neorx Corporation | Prevention and treatment of cardiovascular pathologies |
| US6491938B2 (en) | 1993-05-13 | 2002-12-10 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
| WO1996040098A2 (en) * | 1995-06-07 | 1996-12-19 | Neorx Corporation | Prevention and treatment of cardiovascular pathologies with tamoxifen analogues |
| US6417198B1 (en) | 1993-12-21 | 2002-07-09 | Eli Lilly And Company | Methods of inhibiting CNS problems in post-menopausal women |
| US5478847A (en) | 1994-03-02 | 1995-12-26 | Eli Lilly And Company | Methods of use for inhibiting bone loss and lowering serum cholesterol |
| US5629425A (en) * | 1994-09-19 | 1997-05-13 | Eli Lilly And Company | Haloalkyl hemisolvates of 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-piperidinoethoxy)-benzoyl]benzo[b]thiophene |
| CO4410191A1 (es) | 1994-09-19 | 1997-01-09 | Lilly Co Eli | SINTESIS DE 3-[4-(2-AMINOETOXI)BENZOIL]-2-ARIL-6- HIDROXIBENZO [b] TIOFENOS |
| US6562862B1 (en) | 1994-10-20 | 2003-05-13 | Eli Lilly And Company | Methods of inhibiting physiological conditions associated with an excess of neuropeptide Y |
| US6391892B1 (en) * | 1995-03-10 | 2002-05-21 | Eli Lilly And Company | Naphthyl pharmaceutical compounds |
| IL120266A (en) | 1996-02-28 | 2005-05-17 | Pfizer | Use of estrogen antagonists and estrogen agonists in the preparation of medicaments for inhibiting pathological conditions |
| TW442286B (en) * | 1996-02-28 | 2001-06-23 | Pfizer | New therapeutic uses of estrogen agonists |
| AU5258696A (en) * | 1996-03-19 | 1997-10-10 | Eli Lilly And Company | Synthesis of 3-{4-(2-aminoethoxy)-benzoyl}-2-aryl-6-hydroxy-benzo{b}thiop henes |
| US6465445B1 (en) | 1998-06-11 | 2002-10-15 | Endorecherche, Inc. | Medical uses of a selective estrogen receptor modulator in combination with sex steroid precursors |
| US7005428B1 (en) | 1998-06-11 | 2006-02-28 | Endorecherche, Inc. | Medical uses of a selective estrogen receptor modulator in combination with sex steroid precursors |
| JP4790178B2 (ja) * | 1999-07-06 | 2011-10-12 | アンドルシェルシュ・インコーポレイテッド | 体重増加の処置方法および／または抑制方法 |
| AU7896100A (en) * | 1999-10-14 | 2001-04-23 | Endorecherche Inc. | Selective estrogen receptor modulators in the treatment or reduction of the riskof acquiring hypertension, cardiovascular diseases, and insulin resistance |
| US6613083B2 (en) | 2001-05-02 | 2003-09-02 | Eckhard Alt | Stent device and method |
| US20030216358A1 (en) * | 2001-07-05 | 2003-11-20 | Muchmore Douglas Boyer | Method for enhancing bone mineral density gain |
| RU2198199C1 (ru) * | 2001-09-21 | 2003-02-10 | Закрытое акционерное общество научно-производственная компания "Панджшер-Холдинг" | Способ получения топливных дистиллятов |
| RU2188000C1 (ru) * | 2001-09-27 | 2002-08-27 | Нестерук Владимир Викторович | Лекарственное средство на основе тамоксифена |
| US20060106010A1 (en) * | 2003-05-27 | 2006-05-18 | Black Larry J | Methods for inhibiting bone loss |
| CA2697057A1 (en) * | 2007-08-22 | 2009-02-26 | Gilead Colorado, Inc. | Therapy for complications of diabetes |
| US20120172344A1 (en) * | 2009-07-16 | 2012-07-05 | Kyushu University, National University Corporation | Insulin-producing cell inducer, glucose intake enhancer, and therapeutic agent for diabetes or diabetes complications |
| EP3205648A1 (en) | 2010-06-10 | 2017-08-16 | Seragon Pharmaceuticals, Inc. | Estrogen receptor modulators and uses thereof |
| EP2791132A4 (en) | 2011-12-14 | 2015-08-05 | Seragon Pharmaceuticals Inc | ESTROGEN RECEPTOR MODULATORS AND USES THEREOF |
| EP3493794A4 (en) * | 2016-08-04 | 2020-05-06 | University of Iowa Research Foundation | USE OF SWELL1 INHIBITORS AND MODULATORS FOR TREATING TYPE 2 DIABETES AND ADIPOSITAS |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US2914563A (en) * | 1957-08-06 | 1959-11-24 | Wm S Merrell Co | Therapeutic composition |
| US3274213A (en) * | 1961-09-05 | 1966-09-20 | Upjohn Co | Alkoxy-substituted 2-phenyl-1-(tertiary-aminoalkoxy)phenyl-3, 4-dihydronaphthalenes |
| BE637389A (enExample) * | 1962-09-13 | |||
| US4133814A (en) * | 1975-10-28 | 1979-01-09 | Eli Lilly And Company | 2-Phenyl-3-aroylbenzothiophenes useful as antifertility agents |
| US4230862A (en) * | 1975-10-28 | 1980-10-28 | Eli Lilly And Company | Antifertility compounds |
| US4323707A (en) * | 1975-10-28 | 1982-04-06 | Eli Lilly And Company | Antifertility compounds |
| US4400543A (en) * | 1975-10-28 | 1983-08-23 | Eli Lilly And Company | 3-Phenyl-4-benzoyl-1,2-dihydronaphthalenes |
| US4418068A (en) * | 1981-04-03 | 1983-11-29 | Eli Lilly And Company | Antiestrogenic and antiandrugenic benzothiophenes |
| US4729999A (en) * | 1984-10-12 | 1988-03-08 | Bcm Technologies | Antiestrogen therapy for symptoms of estrogen deficiency |
| US4970237A (en) * | 1987-03-20 | 1990-11-13 | Yale University | Use of clomiphene to increase bone mass in premenopausal women |
| FR2654337B1 (fr) * | 1989-11-15 | 1994-08-05 | Roussel Uclaf | Nouvelles microspheres injectables biodegradables procede de preparation et suspensions injectables les renfermant. |
| DE69023906T2 (de) * | 1990-08-09 | 1996-04-11 | Council Scient Ind Res | Benzopyrane und Verfahren zu deren Herstellung. |
| JPH04312526A (ja) * | 1991-04-09 | 1992-11-04 | Fujisawa Pharmaceut Co Ltd | 骨疾患治療剤 |
| JP3157882B2 (ja) * | 1991-11-15 | 2001-04-16 | 帝国臓器製薬株式会社 | 新規なベンゾチオフエン誘導体 |
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1994
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- 1994-06-20 TW TW083105543A patent/TW275584B/zh active
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- 1994-06-20 ZA ZA944377A patent/ZA944377B/xx unknown
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- 1994-06-20 DK DK94304441.2T patent/DK0635264T3/da active
- 1994-06-20 NZ NZ260790A patent/NZ260790A/en unknown
- 1994-06-20 CZ CZ941520A patent/CZ285522B6/cs not_active IP Right Cessation
- 1994-06-21 NO NO19942363A patent/NO312398B1/no not_active IP Right Cessation
- 1994-06-21 CA CA002126400A patent/CA2126400A1/en not_active Abandoned
- 1994-06-21 PL PL94303937A patent/PL181025B1/pl unknown
- 1994-06-22 AU AU64882/94A patent/AU669627B2/en not_active Ceased
- 1994-06-22 PH PH48503A patent/PH30490A/en unknown
- 1994-06-22 UA UA94005271A patent/UA34441C2/uk unknown
- 1994-06-22 KR KR1019940014148A patent/KR100325034B1/ko not_active Expired - Fee Related
- 1994-06-23 CN CN94107566A patent/CN1086576C/zh not_active Expired - Fee Related
- 1994-06-23 HU HU9401904A patent/HUT75253A/hu unknown
- 1994-06-23 RU RU94022479A patent/RU2132682C1/ru not_active IP Right Cessation
- 1994-06-23 JP JP6141553A patent/JP2886453B2/ja not_active Expired - Fee Related
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1995
- 1995-01-09 US US08/370,062 patent/US5567713A/en not_active Expired - Fee Related
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1997
- 1997-11-07 GR GR970402957T patent/GR3025315T3/el unknown
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |