ZA200200516B - New selective retinoid agonists. - Google Patents
New selective retinoid agonists. Download PDFInfo
- Publication number
- ZA200200516B ZA200200516B ZA200200516A ZA200200516A ZA200200516B ZA 200200516 B ZA200200516 B ZA 200200516B ZA 200200516 A ZA200200516 A ZA 200200516A ZA 200200516 A ZA200200516 A ZA 200200516A ZA 200200516 B ZA200200516 B ZA 200200516B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- hydrogen
- formula
- hexahydro
- tetramethyl
- Prior art date
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- 239000000556 agonist Substances 0.000 title claims description 17
- 150000004492 retinoid derivatives Chemical class 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 81
- 239000001257 hydrogen Substances 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- -1 alkyl-NR'’- Chemical group 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 206010014561 Emphysema Diseases 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 9
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 208000019693 Lung disease Diseases 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- WPQPEFXFZZGKLK-UHFFFAOYSA-N 4-(4,4,7,7-tetramethyl-2,3,5,6-tetrahydro-1h-indene-2-carbonyl)oxybenzoic acid Chemical compound CC1(C)CCC(C)(C)C(C2)=C1CC2C(=O)OC1=CC=C(C(O)=O)C=C1 WPQPEFXFZZGKLK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- PBYRISCIIJHEKW-UHFFFAOYSA-N 4-(2-ethyl-4,4,7,7-tetramethyl-1,3,5,6-tetrahydroindene-2-carbonyl)oxybenzoic acid Chemical compound C1C(C(CCC2(C)C)(C)C)=C2CC1(CC)C(=O)OC1=CC=C(C(O)=O)C=C1 PBYRISCIIJHEKW-UHFFFAOYSA-N 0.000 claims description 3
- IVARBYUKOBABNN-UHFFFAOYSA-N 4-(4,4,7,7-tetramethyl-2-pentyl-1,3,5,6-tetrahydroindene-2-carbonyl)oxybenzoic acid Chemical compound C1C(C(CCC2(C)C)(C)C)=C2CC1(CCCCC)C(=O)OC1=CC=C(C(O)=O)C=C1 IVARBYUKOBABNN-UHFFFAOYSA-N 0.000 claims description 3
- TVFZCPHJOROZLS-UHFFFAOYSA-N 4-[2-(4,4,7,7-tetramethyl-2-pentyl-1,3,5,6-tetrahydroinden-2-yl)ethenyl]benzoic acid Chemical compound C1C(C(CCC2(C)C)(C)C)=C2CC1(CCCCC)C=CC1=CC=C(C(O)=O)C=C1 TVFZCPHJOROZLS-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
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- 239000011664 nicotinic acid Substances 0.000 claims description 3
- XSOUVXLTWXJBFB-UHFFFAOYSA-N 4-[2-(4,4,7,7-tetramethyl-2-pentyl-1,3,5,6-tetrahydroinden-2-yl)ethynyl]benzoic acid Chemical compound C1C(C(CCC2(C)C)(C)C)=C2CC1(CCCCC)C#CC1=CC=C(C(O)=O)C=C1 XSOUVXLTWXJBFB-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000126 substance Substances 0.000 claims 5
- YJWSXCCGZMJIGJ-UHFFFAOYSA-N 2,4,4,7,7-pentamethyl-1,3,5,6-tetrahydroindene-2-carboxylic acid Chemical compound CC1(C)CCC(C)(C)C2=C1CC(C)(C(O)=O)C2 YJWSXCCGZMJIGJ-UHFFFAOYSA-N 0.000 claims 1
- QNJVSEFLRIWKDJ-UHFFFAOYSA-N 4-(2-benzyl-4,4,7,7-tetramethyl-1,3,5,6-tetrahydroindene-2-carbonyl)oxybenzoic acid Chemical compound CC1(C)CCC(C)(C)C(C2)=C1CC2(C(=O)OC=1C=CC(=CC=1)C(O)=O)CC1=CC=CC=C1 QNJVSEFLRIWKDJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
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- 229940096885 Retinoic acid receptor agonist Drugs 0.000 description 8
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/07—Retinol compounds, e.g. vitamin A
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/28—Unsaturated compounds polycyclic
- C07C61/29—Unsaturated compounds polycyclic having a carboxyl group bound to a condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/66—Polycyclic acids with unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99115223 | 1999-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200200516B true ZA200200516B (en) | 2003-06-25 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200200516A ZA200200516B (en) | 1999-08-02 | 2002-01-21 | New selective retinoid agonists. |
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| EP (1) | EP1206436B1 (enExample) |
| JP (1) | JP3961827B2 (enExample) |
| KR (1) | KR100466730B1 (enExample) |
| CN (1) | CN1166618C (enExample) |
| AR (1) | AR024998A1 (enExample) |
| AT (1) | ATE279386T1 (enExample) |
| AU (1) | AU772551B2 (enExample) |
| BR (1) | BR0012951A (enExample) |
| CA (1) | CA2386793C (enExample) |
| DE (1) | DE60014928T2 (enExample) |
| DK (1) | DK1206436T3 (enExample) |
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| MX (1) | MXPA02000828A (enExample) |
| PT (1) | PT1206436E (enExample) |
| TR (1) | TR200200263T2 (enExample) |
| WO (1) | WO2001009076A2 (enExample) |
| ZA (1) | ZA200200516B (enExample) |
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| JO2178B1 (en) * | 1999-10-19 | 2003-04-23 | اف . هوفمان لاروش ايه جي | Treatment of emphysema using rar selective retinoid antagonists |
| US20060161076A1 (en) * | 2005-01-06 | 2006-07-20 | Diamics, Inc. | Systems and methods for collection of cell clusters |
| US20060189893A1 (en) * | 2005-01-06 | 2006-08-24 | Diamics, Inc. | Systems and methods for detecting abnormal cells |
| US7914437B2 (en) * | 2005-02-04 | 2011-03-29 | Ams Research Corporation | Transobturator methods for installing sling to treat incontinence, and related devices |
| US8415390B2 (en) | 2008-05-30 | 2013-04-09 | Microdose Therapeutx, Inc. | Methods and compositions for administration of oxybutynin |
| US9119777B2 (en) | 2008-05-30 | 2015-09-01 | Microdose Therapeutx, Inc. | Methods and compositions for administration of oxybutynin |
| EP2190429B1 (en) | 2007-09-10 | 2016-04-20 | Boston Biomedical, Inc. | A novel group of stat3 pathway inhibitors and cancer stem cell pathway inhibitors |
| DK2547205T3 (da) | 2010-03-19 | 2024-05-27 | 1Globe Biomedical Co Ltd | Hidtil ukendte fremgangsmåder til målretning mod cancerstamceller |
| US8772273B2 (en) * | 2011-10-04 | 2014-07-08 | Quretino Therapeutics, Inc. | Formulations and uses of retinoic acid receptor selective agonists |
| CA2856703A1 (en) | 2011-10-19 | 2013-04-25 | Bikam Pharmaceuticals, Inc. | Opsin-binding ligands, compositions and methods of use |
| US20160030384A1 (en) | 2013-04-09 | 2016-02-04 | Boston Biomedical, Inc. | 2-acetylnaphtho[2,3-b]furan -4,9-dione for use on treating cancer |
| DK3102576T3 (da) | 2014-02-03 | 2019-07-22 | Vitae Pharmaceuticals Llc | Dihydropyrrolopyridininhibitorer af ror-gamma |
| SI3207043T1 (sl) | 2014-10-14 | 2019-04-30 | Vitae Pharmaceuticals, Inc. | Dihidropirolopiridinovi inhibitorji za ROR-gama |
| US9663515B2 (en) | 2014-11-05 | 2017-05-30 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
| EP3331876B1 (en) | 2015-08-05 | 2020-10-07 | Vitae Pharmaceuticals, LLC | Modulators of ror-gamma |
| EP3868750A1 (en) | 2015-11-20 | 2021-08-25 | Vitae Pharmaceuticals, LLC | Modulators of ror-gamma |
| TWI757266B (zh) | 2016-01-29 | 2022-03-11 | 美商維它藥物有限責任公司 | ＲＯＲ－γ調節劑 |
| CA3045306A1 (en) | 2016-11-29 | 2018-06-07 | Boston Biomedical, Inc. | Naphthofuran derivatives, preparation, and methods of use thereof |
| JP2020520923A (ja) | 2017-05-17 | 2020-07-16 | ボストン バイオメディカル， インコーポレイテッド | がんを処置するための方法 |
| WO2019018975A1 (en) | 2017-07-24 | 2019-01-31 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF ROR GAMMA |
| CN115716826A (zh) | 2017-07-24 | 2023-02-28 | 生命医药有限责任公司 | RORγ的抑制剂 |
Family Cites Families (2)
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| LU87821A1 (fr) * | 1990-10-12 | 1992-05-25 | Cird Galderma | Composes bi-aromatiques,et leur utilisation en medecine humaine et veterinaire et en cosmetique |
| US5958954A (en) * | 1995-09-01 | 1999-09-28 | Allergan Sales, Inc. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
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2000
- 2000-07-25 PT PT00951439T patent/PT1206436E/pt unknown
- 2000-07-25 AT AT00951439T patent/ATE279386T1/de not_active IP Right Cessation
- 2000-07-25 MX MXPA02000828A patent/MXPA02000828A/es active IP Right Grant
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- 2000-07-25 TR TR2002/00263T patent/TR200200263T2/xx unknown
- 2000-07-25 DE DE60014928T patent/DE60014928T2/de not_active Expired - Fee Related
- 2000-07-25 KR KR10-2002-7001433A patent/KR100466730B1/ko not_active Expired - Fee Related
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- 2000-07-25 BR BR0012951-8A patent/BR0012951A/pt not_active Application Discontinuation
- 2000-07-25 DK DK00951439T patent/DK1206436T3/da active
- 2000-07-25 EP EP00951439A patent/EP1206436B1/en not_active Expired - Lifetime
- 2000-07-25 JP JP2001514280A patent/JP3961827B2/ja not_active Expired - Fee Related
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2002
- 2002-01-21 ZA ZA200200516A patent/ZA200200516B/en unknown
- 2002-12-19 US US10/323,306 patent/US6828337B2/en not_active Expired - Fee Related
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2004
- 2004-11-02 US US10/979,355 patent/US20050113447A1/en not_active Abandoned
Also Published As
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| AR024998A1 (es) | 2002-11-06 |
| US20030176726A1 (en) | 2003-09-18 |
| WO2001009076A3 (en) | 2001-07-19 |
| CA2386793C (en) | 2006-03-28 |
| TR200200263T2 (tr) | 2004-12-21 |
| US6528677B1 (en) | 2003-03-04 |
| US20050113447A1 (en) | 2005-05-26 |
| ES2228587T3 (es) | 2005-04-16 |
| JP2003526626A (ja) | 2003-09-09 |
| AU772551B2 (en) | 2004-04-29 |
| KR100466730B1 (ko) | 2005-01-24 |
| PT1206436E (pt) | 2004-12-31 |
| ATE279386T1 (de) | 2004-10-15 |
| EP1206436B1 (en) | 2004-10-13 |
| DK1206436T3 (da) | 2005-02-14 |
| MXPA02000828A (es) | 2002-07-30 |
| DE60014928D1 (de) | 2004-11-18 |
| KR20020030089A (ko) | 2002-04-22 |
| EP1206436A2 (en) | 2002-05-22 |
| WO2001009076A2 (en) | 2001-02-08 |
| CN1166618C (zh) | 2004-09-15 |
| CA2386793A1 (en) | 2001-02-08 |
| BR0012951A (pt) | 2002-04-30 |
| DE60014928T2 (de) | 2006-03-09 |
| US6828337B2 (en) | 2004-12-07 |
| AU6437300A (en) | 2001-02-19 |
| JP3961827B2 (ja) | 2007-08-22 |
| CN1368946A (zh) | 2002-09-11 |
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