ZA200301978B - Retinoids for the treatment of emphysema. - Google Patents
Retinoids for the treatment of emphysema. Download PDFInfo
- Publication number
- ZA200301978B ZA200301978B ZA200301978A ZA200301978A ZA200301978B ZA 200301978 B ZA200301978 B ZA 200301978B ZA 200301978 A ZA200301978 A ZA 200301978A ZA 200301978 A ZA200301978 A ZA 200301978A ZA 200301978 B ZA200301978 B ZA 200301978B
- Authority
- ZA
- South Africa
- Prior art keywords
- tetramethyl
- mmol
- tetrahydro
- ethyl acetate
- naphthalen
- Prior art date
Links
- 206010014561 Emphysema Diseases 0.000 title description 77
- 238000011282 treatment Methods 0.000 title description 44
- 150000001875 compounds Chemical class 0.000 claims description 252
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 23
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 11
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- 101100425538 Pseudomonas aeruginosa (strain UCBPP-PA14) tis1 gene Proteins 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 538
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 323
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- -1 retinoid compounds Chemical class 0.000 description 153
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- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
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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
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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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P35/00—Antineoplastic agents
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- 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
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of 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
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of 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 with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/83—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of 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 with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
- C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- 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
- C07C323/51—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 atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/56—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 atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/19—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups having unsaturation outside the aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/28—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
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US20030236301A1 (en) * | 2001-12-19 | 2003-12-25 | Bob Sanders | Liposomal delivery of vitamin E based compounds |
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US7476673B2 (en) * | 2003-12-30 | 2009-01-13 | Allergan, Inc. | Disubstituted chalcone oximes as selective agonists of RARγ retinoid receptors |
GB2411115A (en) * | 2004-02-19 | 2005-08-24 | Medical Res Council | Retinoic acid antagonists for the treatment of oesophageal disorders |
CN100548288C (zh) | 2004-03-10 | 2009-10-14 | 财团法人乙卯研究所 | 记忆固定促进剂 |
WO2007113122A1 (en) * | 2006-03-31 | 2007-10-11 | F. Hoffmann-La Roche Ag | Process for preparing retinoid compounds |
WO2008063842A2 (en) * | 2006-11-02 | 2008-05-29 | Aestus Therapeutics, Inc. | Methods of treating neuropathic pain with agonists of ppar-gamma |
TW201500053A (zh) * | 2008-08-27 | 2015-01-01 | Otsuka Pharma Co Ltd | 用於治療肺部疾病之藥劑(二) |
JP5986570B2 (ja) | 2010-09-01 | 2016-09-06 | トーマス・ジェファーソン・ユニバーシティThomas Jefferson University | 筋修復および再生のための組成物および方法 |
CN109589324B (zh) * | 2012-11-08 | 2022-06-14 | 国立大学法人山口大学 | 角结膜病症的治疗剂 |
KR102303316B1 (ko) | 2013-05-22 | 2021-09-23 | 고쿠리츠다이가쿠호우진 야마구치 다이가쿠 | 망막 맥락막 장해의 억제제 |
EP3098221B1 (en) * | 2014-10-15 | 2017-12-06 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Process for preparing apixaban form n-1 |
EP4098257A1 (en) | 2015-11-25 | 2022-12-07 | IO Therapeutics, Inc. | Use of cyp26-resistant rar alpha selective agonists in the treatment of cancer |
EA201892497A1 (ru) | 2016-06-08 | 2019-05-31 | Клементиа Фармасьютикалз Инк. | Способы лечения гетеротопической оссификации |
CN109310763B (zh) | 2016-06-10 | 2022-10-21 | Io治疗公司 | 用于癌症免疫疗法的受体选择性类视黄醇和rexinoid化合物和免疫调节剂 |
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CN110381939B (zh) | 2016-11-16 | 2022-12-02 | 同理制药公司 | 用于治疗多发性骨软骨瘤(mo)的方法 |
AU2018298193A1 (en) | 2017-07-06 | 2020-01-02 | Jiangsu Hengrui Medicine Co., Ltd. | Indole-formamide derivative, preparation method therefor and use thereof in medicine |
MX2020000467A (es) | 2017-07-13 | 2020-08-03 | Io Therapeutics Inc | Compuestos retinoides y rexinoides inmunomoduladores en combinacion con inmunomoduladores para inmunoterapia contra cancer. |
KR20200044889A (ko) | 2017-08-31 | 2020-04-29 | 아이오 테라퓨틱스, 인크. | 암 면역요법을 위해 면역 조절제와 조합된 rar 선택적 작용제 |
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CN115073394A (zh) * | 2022-06-29 | 2022-09-20 | 上海中医药大学 | 一种高烯丙基类化合物及其制备方法和应用 |
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US5527945A (en) | 1989-02-10 | 1996-06-18 | Basf Aktiengesellschaft | Diphenylheteroalkyl derivatives, the preparation thereof and drugs and cosmetics prepared therefrom |
US5324840A (en) | 1992-06-11 | 1994-06-28 | Allergan, Inc. | Method of treatment with compounds having retinoid-like activity and reduced skin toxicity and lacking teratogenic effects |
MX9306629A (es) * | 1993-01-11 | 1994-07-29 | Ligand Pharm Inc | Compuestos que tienen actividad selectiva para receptores retinoide x, medios para modulacion de procesos mediados pr receptores de retinoide x. |
CA2129773C (en) * | 1993-09-02 | 2007-05-01 | Michael Klaus | Aromatic carboxylic acid derivatives |
AU2823395A (en) | 1994-06-07 | 1996-01-04 | Sri International | Novel compounds useful in modulating gene expression of retinoid responsive genes and/or having anti-ap-1 activity |
ATE223713T1 (de) | 1995-04-10 | 2002-09-15 | Taiho Pharmaceutical Co Ltd | Inhibitor der krebsmetastasierung |
US5965606A (en) * | 1995-12-29 | 1999-10-12 | Allergan Sales, Inc. | Methods of treatment with compounds having RAR.sub.α receptor specific or selective activity |
FR2746098B1 (fr) | 1996-03-14 | 1998-04-30 | Composes propynyl biaromatiques | |
FR2753091B1 (fr) | 1996-09-09 | 2001-03-16 | Oreal | Utilisation d'un agoniste des recepteurs des retinoides de type rxr pour stimuler ou induire la pousse des cheveux et/ou stopper leur chute |
US5998486A (en) * | 1997-07-08 | 1999-12-07 | Georgetown University School Of Medicine | Treatment of emphysema with retinoic acid or other retinoids by inducing formation of gas-exchange units (alveoli) |
TWI281911B (en) * | 2000-04-04 | 2007-06-01 | Allergan Inc | Treatment of tumors with RARalpha selective retinoid compounds in combination with other anti-tumor agents |
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2001
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- 2001-09-24 KR KR1020037004742A patent/KR100682144B1/ko active IP Right Grant
- 2001-09-24 HU HU0303006A patent/HU230063B1/hu unknown
- 2001-09-24 PL PL362671A patent/PL208665B1/pl unknown
- 2001-09-24 DE DE60136477T patent/DE60136477D1/de not_active Expired - Lifetime
- 2001-09-24 CA CA2422805A patent/CA2422805C/en not_active Expired - Lifetime
- 2001-09-24 RS YUP-244/03A patent/RS50354B/sr unknown
- 2001-09-24 SI SI200130886T patent/SI1324970T1/sl unknown
- 2001-09-24 DK DK01969762T patent/DK1324970T3/da active
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- 2001-09-24 NZ NZ524603A patent/NZ524603A/en not_active IP Right Cessation
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- 2001-09-24 AU AU2001289913A patent/AU2001289913B2/en not_active Expired
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- 2001-09-24 AU AU8991301A patent/AU8991301A/xx active Pending
- 2001-09-24 AT AT01969762T patent/ATE413375T1/de active
- 2001-09-27 JO JO2001155A patent/JO2434B1/en active
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- 2001-09-28 PA PA20018529701A patent/PA8529701A1/es unknown
- 2001-10-01 US US09/968,425 patent/US6777418B2/en not_active Expired - Lifetime
- 2001-10-02 GT GT200100199A patent/GT200100199A/es unknown
- 2001-10-02 TW TW090124279A patent/TWI304805B/zh not_active IP Right Cessation
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2003
- 2003-03-06 IL IL154810A patent/IL154810A/en active IP Right Grant
- 2003-03-11 ZA ZA200301978A patent/ZA200301978B/en unknown
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- 2003-04-01 NO NO20031480A patent/NO329113B1/no not_active IP Right Cessation
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2004
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2009
- 2009-01-22 CY CY20091100085T patent/CY1109045T1/el unknown
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