CA2842106A1 - Cysteine prodrugs - Google Patents
Cysteine prodrugs Download PDFInfo
- Publication number
- CA2842106A1 CA2842106A1 CA2842106A CA2842106A CA2842106A1 CA 2842106 A1 CA2842106 A1 CA 2842106A1 CA 2842106 A CA2842106 A CA 2842106A CA 2842106 A CA2842106 A CA 2842106A CA 2842106 A1 CA2842106 A1 CA 2842106A1
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- CA
- Canada
- Prior art keywords
- group
- compound
- disease
- formula
- pharmaceutically acceptable
- 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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- 239000000651 prodrug Substances 0.000 title claims abstract description 19
- 229940002612 prodrug Drugs 0.000 title claims abstract description 19
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 title abstract description 23
- 235000018417 cysteine Nutrition 0.000 title abstract description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 36
- 201000010099 disease Diseases 0.000 claims abstract description 25
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 22
- 206010013663 drug dependence Diseases 0.000 claims abstract description 18
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 17
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims abstract description 13
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 9
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 9
- 208000020925 Bipolar disease Diseases 0.000 claims abstract description 9
- 206010012289 Dementia Diseases 0.000 claims abstract description 9
- 208000023105 Huntington disease Diseases 0.000 claims abstract description 9
- 208000032382 Ischaemic stroke Diseases 0.000 claims abstract description 9
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 9
- 230000036506 anxiety Effects 0.000 claims abstract description 9
- 208000010877 cognitive disease Diseases 0.000 claims abstract description 9
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 9
- 208000011117 substance-related disease Diseases 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 89
- 150000002148 esters Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims description 16
- 229960004308 acetylcysteine Drugs 0.000 claims description 14
- 239000000164 antipsychotic agent Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 235000001014 amino acid Nutrition 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
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- VSWBSWWIRNCQIJ-GJZGRUSLSA-N (R,R)-asenapine Chemical compound O1C2=CC=CC=C2[C@@H]2CN(C)C[C@H]2C2=CC(Cl)=CC=C21 VSWBSWWIRNCQIJ-GJZGRUSLSA-N 0.000 claims description 3
- BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 claims description 3
- PXUIZULXJVRBPC-UHFFFAOYSA-N 1'-[3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl]hexahydro-2H-spiro[imidazo[1,2-a]pyridine-3,4'-piperidin]-2-one Chemical compound C12=CC(Cl)=CC=C2CCC2=CC=CC=C2N1CCCN1CCC2(C(NC3CCCCN32)=O)CC1 PXUIZULXJVRBPC-UHFFFAOYSA-N 0.000 claims description 3
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- PMXMIIMHBWHSKN-UHFFFAOYSA-N 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCC(O)C4=NC=3C)=NOC2=C1 PMXMIIMHBWHSKN-UHFFFAOYSA-N 0.000 claims description 3
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims description 3
- CYGODHVAJQTCBG-UHFFFAOYSA-N Bifeprunox Chemical compound C=12OC(=O)NC2=CC=CC=1N(CC1)CCN1CC(C=1)=CC=CC=1C1=CC=CC=C1 CYGODHVAJQTCBG-UHFFFAOYSA-N 0.000 claims description 3
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- KAAZGXDPUNNEFN-UHFFFAOYSA-N Clotiapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2SC2=CC=C(Cl)C=C12 KAAZGXDPUNNEFN-UHFFFAOYSA-N 0.000 claims description 3
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 claims description 3
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- RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 claims description 3
- KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 claims description 3
- GFBKORZTTCHDGY-UWVJOHFNSA-N Thiothixene Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2\C1=C\CCN1CCN(C)CC1 GFBKORZTTCHDGY-UWVJOHFNSA-N 0.000 claims description 3
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- NTJOBXMMWNYJFB-UHFFFAOYSA-N amisulpride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC NTJOBXMMWNYJFB-UHFFFAOYSA-N 0.000 claims description 3
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- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 claims description 3
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- 229960003864 clotiapine Drugs 0.000 claims description 3
- 229960004170 clozapine Drugs 0.000 claims description 3
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims description 3
- RMEDXOLNCUSCGS-UHFFFAOYSA-N droperidol Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CC=C(N2C(NC3=CC=CC=C32)=O)CC1 RMEDXOLNCUSCGS-UHFFFAOYSA-N 0.000 claims description 3
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- XMXHEBAFVSFQEX-UHFFFAOYSA-N iloperidone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C=2C3=CC=C(F)C=C3ON=2)CC1 XMXHEBAFVSFQEX-UHFFFAOYSA-N 0.000 claims description 3
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- XJGVXQDUIWGIRW-UHFFFAOYSA-N loxapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 XJGVXQDUIWGIRW-UHFFFAOYSA-N 0.000 claims description 3
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- PQXKDMSYBGKCJA-CVTJIBDQSA-N lurasidone Chemical compound C1=CC=C2C(N3CCN(CC3)C[C@@H]3CCCC[C@H]3CN3C(=O)[C@@H]4[C@H]5CC[C@H](C5)[C@@H]4C3=O)=NSC2=C1 PQXKDMSYBGKCJA-CVTJIBDQSA-N 0.000 claims description 3
- SLVMESMUVMCQIY-UHFFFAOYSA-N mesoridazine Chemical compound CN1CCCCC1CCN1C2=CC(S(C)=O)=CC=C2SC2=CC=CC=C21 SLVMESMUVMCQIY-UHFFFAOYSA-N 0.000 claims description 3
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- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims description 3
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- 229960004431 quetiapine Drugs 0.000 claims description 3
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 claims description 3
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- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims description 3
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- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 claims description 3
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/19—Carboxylic acids, e.g. valproic acid
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- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/10—Seven-membered rings having the hetero atoms in positions 1 and 4 not condensed with other rings
-
- 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
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings 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
- C07D277/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
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- Epidemiology (AREA)
- Psychiatry (AREA)
- Molecular Biology (AREA)
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- Virology (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Oncology (AREA)
- Addiction (AREA)
- Psychology (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161512751P | 2011-07-28 | 2011-07-28 | |
| US61/512,751 | 2011-07-28 | ||
| PCT/US2012/048820 WO2013016727A1 (en) | 2011-07-28 | 2012-07-30 | Cysteine prodrugs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2842106A1 true CA2842106A1 (en) | 2013-01-31 |
Family
ID=47601579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2842106A Pending CA2842106A1 (en) | 2011-07-28 | 2012-07-30 | Cysteine prodrugs |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US9457014B2 (enExample) |
| EP (1) | EP2736890A4 (enExample) |
| JP (1) | JP2014524936A (enExample) |
| CA (1) | CA2842106A1 (enExample) |
| WO (1) | WO2013016727A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013016727A1 (en) * | 2011-07-28 | 2013-01-31 | Promentis Pharmaceuticals, Inc. | Cysteine prodrugs |
| US20130338165A1 (en) * | 2012-06-15 | 2013-12-19 | Promentis Pharmaceuticals, Inc. | Use of Compounds Elevating Glutathione Levels for the Treatment of Parkinson's Disease |
| US20150045312A1 (en) * | 2013-08-12 | 2015-02-12 | Promentis Pharmaceuticals, Inc. | Use of Compounds Elevating Glutathione Levels for the Treatment of Autism, Autistic Spectrum Disorders and Fragile X Syndrome |
| LT3066089T (lt) | 2013-11-08 | 2020-02-25 | Promentis Pharmaceuticals, Inc. | Pakeistieji n-acetil-l-cisteino dariniai ir giminingi junginiai |
| EP3194027B1 (en) * | 2014-09-15 | 2026-02-11 | Sound Pharmaceuticals Incorporated | Compositions for use in treating psychotic disorders |
| HUE069280T2 (hu) | 2016-05-18 | 2025-02-28 | Sound Pharmaceuticals Incorporated | Ebselen a Meniere-kór kezelésére történõ felhasználásra |
| ES3001152T3 (es) | 2016-12-20 | 2025-03-04 | Lts Lohmann Therapie Systeme Ag | Sistema terapéutico transdérmico que contiene asenapina y polisiloxano o poliisobutileno |
| PL3338768T3 (pl) | 2016-12-20 | 2020-05-18 | Lts Lohmann Therapie-Systeme Ag | Transdermalny system terapeutyczny zawierający asenapinę |
| WO2019002204A1 (en) | 2017-06-26 | 2019-01-03 | Lts Lohmann Therapie-Systeme Ag | TRANSDERMAL THERAPEUTIC SYSTEM CONTAINING ASENAPINE AND SILICONE-TYPE ACRYLIC HYBRID POLYMER |
| WO2019113084A1 (en) | 2017-12-05 | 2019-06-13 | Sunovion Pharmaceuticals Inc. | Crystal forms and production methods thereof |
| CN118593482A (zh) | 2017-12-05 | 2024-09-06 | 赛诺维信制药公司 | 非外消旋混合物及其用途 |
| AU2019291060B2 (en) | 2018-06-20 | 2024-09-05 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine |
| EP3810099A1 (en) | 2018-06-20 | 2021-04-28 | LTS Lohmann Therapie-Systeme AG | Transdermal therapeutic system containing asenapine |
| WO2020142450A1 (en) * | 2018-12-31 | 2020-07-09 | Zymergen Inc. | Polymer compositions comprising compounds derived from biology |
| MX2021014774A (es) | 2019-06-04 | 2022-02-03 | Sunovion Pharmaceuticals Inc | Formulaciones de liberacion modificada y usos de las mismas. |
| CN113024473B (zh) * | 2021-04-13 | 2022-08-23 | 陕西慧康生物科技有限责任公司 | 一种含有半胱氨酸的环二肽的合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT995110B (it) * | 1973-08-01 | 1975-11-10 | Snam Progetti | Procedimento per la produzione di composti eterociclici e prodotti ottenuti |
| JPS6016989A (ja) * | 1983-07-06 | 1985-01-28 | Shionogi & Co Ltd | オキソ飽和異項環カルボンアミドセフエム化合物 |
| US5298516A (en) * | 1991-03-27 | 1994-03-29 | Sankyo Company, Limited | Thiazolidone compounds and method of using the same as a vasodilator |
| AU682894B2 (en) | 1993-10-28 | 1997-10-23 | Institut National De La Recherche Agronomique | Composition based on amino acids intended for the treatment of sepsis or of an attack bringing about an inflammatory reaction, in animals and man |
| US6413999B1 (en) * | 1999-08-17 | 2002-07-02 | University Of Saskatchewan Technologies Inc. | Treatment for acute physical insult to the central nervous system |
| US7829709B1 (en) * | 2007-08-10 | 2010-11-09 | Marquette University | Cysteine prodrugs to treat schizophrenia and drug addiction |
| EP2252596B1 (en) * | 2008-02-07 | 2016-12-28 | Marquette University | Cysteine and cystine prodrugs to treat schizophrenia and reduce drug cravings |
| WO2013016727A1 (en) * | 2011-07-28 | 2013-01-31 | Promentis Pharmaceuticals, Inc. | Cysteine prodrugs |
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2012
- 2012-07-30 WO PCT/US2012/048820 patent/WO2013016727A1/en not_active Ceased
- 2012-07-30 JP JP2014523106A patent/JP2014524936A/ja active Pending
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2016
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Also Published As
| Publication number | Publication date |
|---|---|
| US20160081987A1 (en) | 2016-03-24 |
| EP2736890A1 (en) | 2014-06-04 |
| JP2014524936A (ja) | 2014-09-25 |
| EP2736890A4 (en) | 2015-07-15 |
| US20160287563A1 (en) | 2016-10-06 |
| US9457014B2 (en) | 2016-10-04 |
| WO2013016727A1 (en) | 2013-01-31 |
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