CA2415169C - Novel c-4 substituted retinoids - Google Patents
Novel c-4 substituted retinoids Download PDFInfo
- Publication number
- CA2415169C CA2415169C CA2415169A CA2415169A CA2415169C CA 2415169 C CA2415169 C CA 2415169C CA 2415169 A CA2415169 A CA 2415169A CA 2415169 A CA2415169 A CA 2415169A CA 2415169 C CA2415169 C CA 2415169C
- Authority
- CA
- Canada
- Prior art keywords
- atra
- group
- retinoic acid
- pharmaceutical composition
- compound
- 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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- SHGAZHPCJJPHSC-YCNIQYBTSA-N retinoic acid group Chemical class C\C(=C/C(=O)O)\C=C\C=C(\C=C\C1=C(CCCC1(C)C)C)/C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims abstract description 235
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- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 8
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- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 229960003471 retinol Drugs 0.000 description 1
- 235000020944 retinol Nutrition 0.000 description 1
- 239000011607 retinol Substances 0.000 description 1
- 102000029752 retinol binding Human genes 0.000 description 1
- 108091000053 retinol binding Proteins 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
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- 238000004611 spectroscopical analysis Methods 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
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- 230000009885 systemic effect Effects 0.000 description 1
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- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 238000006257 total synthesis reaction Methods 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
- VYNGFCUGSYEOOZ-UHFFFAOYSA-N triphenylphosphine sulfide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=S)C1=CC=CC=C1 VYNGFCUGSYEOOZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- 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
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/61—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
- C07D331/02—Three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21746500P | 2000-07-11 | 2000-07-11 | |
| US60/217,465 | 2000-07-11 | ||
| PCT/US2001/016524 WO2002003912A2 (en) | 2000-07-11 | 2001-07-11 | Novel c-4 substituted retinoids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2415169A1 CA2415169A1 (en) | 2002-01-17 |
| CA2415169C true CA2415169C (en) | 2010-06-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2415169A Expired - Fee Related CA2415169C (en) | 2000-07-11 | 2001-07-11 | Novel c-4 substituted retinoids |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7265143B2 (https=) |
| EP (1) | EP1305274A4 (https=) |
| JP (1) | JP2004509073A (https=) |
| AU (2) | AU2001271265B2 (https=) |
| CA (1) | CA2415169C (https=) |
| WO (1) | WO2002003912A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040242689A1 (en) * | 1999-08-26 | 2004-12-02 | Parks L. Dean | Method of treating benign prostatic hyperplasia and other benign prostate conditions |
| US20050107352A1 (en) * | 1999-08-26 | 2005-05-19 | Parks L. D. | Method of treating benign prostatic hyperplasia |
| FR2894465B1 (fr) | 2005-12-14 | 2010-09-10 | Fabre Pierre Dermo Cosmetique | Utilisation de composes polyinsatures en tant qu'agents blanchissants |
| FR2894577B1 (fr) * | 2005-12-14 | 2008-02-22 | Fabre Pierre Dermo Cosmetique | Nouveaux composes polyinsatures, leur procede de preparation et les compositions les contenant. |
| EP2167090A4 (en) | 2007-06-06 | 2010-08-25 | Univ Maryland | HDAC INHIBITORS AND HORMONE TREATMENT MEDICAMENTS |
| US20100184812A1 (en) * | 2007-06-06 | 2010-07-22 | University Of Maryland, Baltimore | Mutual prodrugs and methods to treat cancer |
| WO2010036404A2 (en) * | 2008-05-09 | 2010-04-01 | University Of Maryland, Baltimore | Novel retinamide retinoic acid metabolism blocking agents |
| WO2011016863A2 (en) * | 2009-08-05 | 2011-02-10 | Angion Biomedica Corp. | Methods and uses of cytochrome p450 inhibitors |
| US10414760B2 (en) | 2016-11-29 | 2019-09-17 | Angion Biomedica Corp. | Cytochrome P450 inhibitors and uses thereof |
| CN102985420B (zh) | 2010-06-01 | 2017-07-04 | 安吉翁生物医药有限公司 | 细胞色素p450抑制剂及其用途 |
| WO2013028771A1 (en) | 2011-08-23 | 2013-02-28 | Leong Hwei Xian | Reversing intestinal inflammation by inhibiting retinoic acid metabolism |
| WO2014093960A1 (en) * | 2012-12-16 | 2014-06-19 | Angion Biomedica Corp. | Compositions and methods for treating disease |
| CA2957785C (en) | 2014-08-11 | 2023-01-03 | Angion Biomedica Corporation | Cytochrome p450 inhibitors and uses thereof |
| WO2016081589A2 (en) | 2014-11-20 | 2016-05-26 | University Of Maryland, Baltimore | 13-cis-ramba retinamides that degrade mnks for treating cancer |
| JP2018501279A (ja) | 2014-12-31 | 2018-01-18 | アンギオン バイオメディカ コーポレイション | 疾患を治療するための方法及び薬剤 |
| CN109675256B (zh) * | 2019-03-02 | 2023-05-23 | 哈尔滨理工大学 | 一种内齿啮合式乳腺癌术后康复训练装置及使用方法 |
| US12528776B2 (en) * | 2019-12-19 | 2026-01-20 | University Of Maryland, Baltimore | Composition and method for treating dermatological disorders using retinamides |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4169103A (en) * | 1978-04-12 | 1979-09-25 | Hoffmann-La Roche Inc. | Nonatetraenoic acid derivatives |
| US5124083A (en) * | 1990-08-30 | 1992-06-23 | Southern Research Institute | 3-substituted and 3,3-disubstituted 4-oxoretinoic acids and their esters |
| US5808120A (en) * | 1995-08-22 | 1998-09-15 | Wisconsin Alumni Research Foundation | Method of synthesis of retinoic acid |
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2001
- 2001-07-11 WO PCT/US2001/016524 patent/WO2002003912A2/en not_active Ceased
- 2001-07-11 JP JP2002508369A patent/JP2004509073A/ja active Pending
- 2001-07-11 CA CA2415169A patent/CA2415169C/en not_active Expired - Fee Related
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2007
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Also Published As
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| CA2415169A1 (en) | 2002-01-17 |
| AU2001271265B2 (en) | 2005-01-06 |
| EP1305274A4 (en) | 2005-10-12 |
| WO2002003912A2 (en) | 2002-01-17 |
| US20030162823A1 (en) | 2003-08-28 |
| US20120122908A1 (en) | 2012-05-17 |
| JP2004509073A (ja) | 2004-03-25 |
| EP1305274A2 (en) | 2003-05-02 |
| US7265143B2 (en) | 2007-09-04 |
| AU7126501A (en) | 2002-01-21 |
| WO2002003912A3 (en) | 2002-07-18 |
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| EEER | Examination request | ||
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