HRP20220764T1 - Psma ligandi za snimanje i endoradioterapiju - Google Patents
Psma ligandi za snimanje i endoradioterapiju Download PDFInfo
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- HRP20220764T1 HRP20220764T1 HRP20220764TT HRP20220764T HRP20220764T1 HR P20220764 T1 HRP20220764 T1 HR P20220764T1 HR P20220764T T HRP20220764T T HR P20220764TT HR P20220764 T HRP20220764 T HR P20220764T HR P20220764 T1 HRP20220764 T1 HR P20220764T1
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- Prior art keywords
- group
- bond
- compound
- oligo
- optionally substituted
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- 238000003384 imaging method Methods 0.000 title 1
- 239000003446 ligand Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- 239000004202 carbamide Substances 0.000 claims 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 230000002285 radioactive effect Effects 0.000 claims 4
- -1 substituted Chemical class 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 125000000732 arylene group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 102220632799 Immunoglobulin heavy variable 1-69_R11A_mutation Human genes 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010029113 Neovascularisation Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 238000003745 diagnosis Methods 0.000 claims 1
- 239000003550 marker Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229920002601 oligoester Polymers 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0482—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group chelates from cyclic ligands, e.g. DOTA
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2121/00—Preparations for use in therapy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Optics & Photonics (AREA)
- Epidemiology (AREA)
- Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Nuclear Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (15)
1. Spoj formule (I), ili njegova farmaceutski prihvatljiva sol,
[image]
naznačeno time, što:
m je cijeli broj od 2 do 6;
n je cijeli broj od 2 do 6;
R1L je CH2, NH ili O;
R2L je C ili P(OH);
R3L je CH2, NH ili O;
X1 je odabran između amidne veze, eterske veze, tioeterske veze, esterske veze, tioesterske veze, urea mosta i aminske veze;
L1 je dvovalentna vezna skupina sa strukturom odabranom između oligoamida, oligoetera, oligotioetera, oligoestera, oligotioestera, oligouree, oligo(eter-amida), oligo(tioeter-amida), oligo(esteramida), oligo(tioester-amid), oligo(urea-amid), oligo(eter-tioeter), oligo(eter-ester), oligo(eter-tioester), oligo(eter-urea), oligo (tioeter-ester), oligo(tioeter-tioester), oligo(tioeter- urea), oligo(ester-tioester), oligo(ester-urea) i oligo(tioester-urea), koja vezna grupa može nositi grupni EDS;
X2 se bira između amidne veze, eterske veze, tioeterske veze, esterske veze, tioesterske veze, urea mosta i aminske veze;
R2 je izborno supstituirana arilna skupina ili izborno supstituirana aralkilna skupina, koja arilna skupina ili aralkilna skupina može biti supstituirana na svom aromatskom prstenu s jednim ili više supstituenata odabranih između halogena i -OH;
R3 je izborno supstituirana arilna skupina ili izborno supstituirana aralkilna skupina, koja arilna skupina ili aralkilna skupina može biti supstituirana na svom aromatskom prstenu s jednim ili više supstituenata odabranih između halogena i -OH;
r je 0 ili 1;
p je 0 ili 1;
q je 0 ili 1;
R4 se bira između izborno supstituirane arilne skupine i skupine EDS, koja arilna skupina može biti supstituirana na svom aromatičnom prstenu s jednim ili više supstituenata odabranih između halogena, -OH i -NH2;
X3 se bira između amidne veze, eterske veze, tioeterske veze, esterske veze, tioesterske veze, urea mosta, aminske veze i grupe formule
[image]
pri čemu označena veza na karbonilnoj skupini veže X3 za RM, a druga označena veza veže X3 za ostatak spoja formule (I);
RM je markerska skupina koja sadrži kelirajuću skupinu koja izborno sadrži kelirani neradioaktivni ili radioaktivni kation;
i pri čemu je skupina EDS barem jednom sadržana u spoju formule (I) i ima strukturu odabranu između (E-1A), (E-1B), (E-2A) i (E-2B):
[image]
pri čemu
[image]
označava vezu koja veže skupinu EDS, na ostatak spoja formule (I);
s je 1, 2 ili 3, poželjno 1 ili 2, a još poželjnije 1;
t je 1, 2 ili 3, poželjno 1 ili 2, a još poželjnije 2;
R5A je, neovisno za svaku pojavu za s > 1, supstituent za povlačenje elektrona, koji je poželjno odabran između -NO2 i -COOH, a koji je poželjnije -COOH, i pri čemu veza između R5A i fenilnog prstena pokazuje da s skupine R5A zamjenjuju s atome vodika na bilo kojem položaju na fenilnom prstenu;
R5B je, neovisno za svaku pojavu za s > 1, supstituent koji nosi usamljeni par elektrona na atomu izravno vezan na fenilni prsten prikazan u formuli (E-1B), a koji je supstituent poželjno odabran između -OH i -NH2, i što je poželjnije -NH2, i pri čemu veza između R5B i fenilnog prstena pokazuje da s skupine R5B zamjenjuju s atome vodika na bilo kojem položaju na fenilnom prstenu; R6A je, neovisno za svaku pojavu za t > 1, supstituent za povlačenje elektrona, koji je poželjno odabran između -NO2 i -COOH, a koji je poželjnije -COOH, i pri čemu veza između R6A i fenilnog prstena pokazuje da t skupine R6A zamjenjuju t atome vodika na bilo kojem položaju na fenilnom prstenu; i R6B je, neovisno za svaku pojavu za t > 1, supstituent koji nosi usamljeni par elektrona na atomu izravno vezan na fenilni prsten prikazan u formuli (E-1B), a koji je supstituent poželjno odabran između -OH i -NH2, a koji je poželjnije -OH, i pri čemu veza između R6B i fenilnog prstena ukazuje da t skupine R6B zamjenjuju t atome vodika na bilo kojem položaju na fenilnom prstenu.
2. Spoj ili sol u skladu s patentnim zahtjevom 1, naznačeno time, da m je 2, n je 2 ili 4, R1L je NH, R2L je C, a R3L je NH.
3. Spoj ili sol u skladu s patentnim zahtjevom 1 ili 2, naznačeno time, što je L1 dvovalentna vezna skupina sa strukturom odabranom od oligoamida koji sadrži ukupno 1 do 5, poželjnije ukupno 1 do 3, a najpoželjnije ukupno 1 ili 2 amidne veze unutar svoje okosnice i oligo(ester-amid) koji sadrži ukupno 2 do 5, poželjnije ukupno 2 do 3, a najpoželjnije ukupno 2 amidne i esterske veze unutar svoje okosnice, koje povezuju grupa može nositi grupni EDS.
4. Spoj ili sol u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačeno time, što dio -X2-L1-X1- u formuli (I) ima strukturu odabranu od:
*-C(O)-NH-R7-NH-C(O)-R8-C(O)-NH- (L-1),
*-C(O)-NH-R9A-NH-C(O)-R10A-C(O)-NH-R11A-NH-C(O)- (L-2A),
i
*-C(O)-NH-R9B-C(O)-NH-R10B-C(O)-NH-R11B-NH-C(O)- (L-2B);
pri čemu je amidna veza označena sa * vezana na atom ugljika koji nosi R2 u formuli (I), i gdje
R7, R8, R9A, R9B, R11A i R11B su neovisno odabrani između izborno supstituiranog C2 do C10 alkandiila, od kojih svaka alkandiilna skupina može biti supstituirana s jednim ili više supstituenata neovisno odabranih između -OH, -OCH3, -COOH, -COOCH3, - NH2, - NHC(NH)NH2, i grupa EDS, i C10 arenediil, od kojih alkandiil i arenediil grupa mogu biti supstituirane s jednim ili više supstituenata neovisno odabranih između -OH, -OCH3, -COOH, -COOCH3, -NH2, -NHC(NH)NH2, i grupa EDS.
5. Spoj ili sol u skladu s patentnim zahtjevom 4, naznačeno time, što dio -X2-L1-X1- ima strukturu odabranu od:
*-C(O)-NH-CH(COOH)-R12-NH-C(O)-R13-C(O)-NH-(L-3), *-C(O)-NH-CH(COOH)-R14-NH-C(O)-R15-C(O)-NH-R16-CH(COOH)-NH-C(O)-(L-4 ),
i
*-C(O)-NH-CH(COOH)-R17-C(O)-NH-R18-C(O)-NH-R19-CH(COOH)-NH-C(O)-(L-5 );
pri čemu je veza koja je označena sa * vezana na atom ugljika koji nosi R2 u formuli (I),
R12 i R14 su neovisno odabrani između ravnog C2 do C6 alkandiila,
R13 je ravni C2 do C10 alkandiil,
R15 i R16 su neovisno odabrani između ravnog C2 do C6 alkandiila,
i pri čemu svaki od R13 i R15 može nositi jednu skupinu EDS kao supstituent,
R17 je ravni C2 do C6 alkandiil,
R18 je fenilenska skupina, i
R19 je ravni C2 do C6 alkandiil.
6. Spoj ili sol u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačeno time, što je R2 je po izboru supstituirana aralkilna skupina odabrana od po izboru supstituiranog -CH2-fenila i po izboru supstituiranog -CH2-naftila, pri čemu su fenil i naftilna skupina po izboru supstituirani s odabranim supstituentom od halogena, poželjno I, i -OH.
7. Spoj ili sol u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačeno time, gdje je R3 po izboru supstituirana aralkilna skupina, po izboru odabrana od supstituiranog -CH2-fenila i po izboru supstituiranog -CH2-naftila, pri čemu su fenil i naftilna skupina po izboru supstituirane s odabranim supstituentom od halogena i -OH.
8. Spoj ili sol u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačeno time, gdje je r 1, i gdje je R4 odabran između izborno supstituiranog fenila, izborno supstituiranog naftila i grupe EDS, pri čemu su fenilna skupina i naftilna skupina po izboru supstituirane sa supstituentom odabranim od halogena, -OH i -NH2.
9. Spoj ili sol u skladu s bilo kojim od patentnih zahtjeva 1 do 8, naznačeno time, što je X3 amidna veza ili skupina formule
[image]
pri čemu označena veza na karbonilnoj skupini veže X3 za RM, a druga označena veza veže X3 za ostatak molekule.
10. Spoj ili sol u skladu bilo kojim od patentnih zahtjeva 1 do 9, naznačeno time, da RM je kelatna skupina koja izborno sadrži kelirani neradioaktivni ili radioaktivni kation.
11. Spoj ili sol u skladu s bilo kojim patentnim zahtjevom od 1 do 10, naznačeno time, da spoj formule (I) ili sadrži jednu skupinu EDS koju nosi vezna skupina L1, ili sadrži dvije skupine EDS, od kojih je jedna predstavljena s R4, a druga se nosi s L1.
12. Spoj ili sol u skladu s bilo kojim od patentnih zahtjeva 1 do 11, naznačeno time, što sadrži skupinu EDS koja ima formulu (E-2A):
[image]
pri čemu
[image]
[image]
označava vezu koja veže skupinu EDS na ostatak spoja formule (I); i
t je 1 ili 2, a R6A se bira između -NO2 i -COOH.
13. Spoj ili njegova sol u skladu s bilo kojim patentnim zahtjevom 1 do 12, naznačeno time, što navedeni spoj ili sol imaju jedno od sljedećih formula:
[image]
[image]
[image]
14. Farmaceutski ili dijagnostički pripravak, naznačeno time, što sadrži ili se sastoji od jednog ili više spojeva ili soli u skladu s bilo kojim od patentnih zahtjeva 1 do 13.
15. Spoj ili njegova sol u skladu s bilo kojim od patentnih zahtjeva 1 do 13, naznačeno time, što se koristi u postupku dijagnosticiranja i/ili liječenja
(a) karcinoma uključujući karcinom prostate; ili
(b) neoangiogeneze/angiogeneze.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17206510 | 2017-12-11 | ||
| EP18812215.4A EP3723815B1 (en) | 2017-12-11 | 2018-12-11 | Psma ligands for imaging and endoradiotherapy |
| PCT/EP2018/084399 WO2019115547A1 (en) | 2017-12-11 | 2018-12-11 | Psma ligands for imaging and endoradiotherapy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20220764T1 true HRP20220764T1 (hr) | 2022-09-16 |
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ID=60654872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20220764TT HRP20220764T1 (hr) | 2017-12-11 | 2018-12-11 | Psma ligandi za snimanje i endoradioterapiju |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US11497819B2 (hr) |
| EP (2) | EP3723815B1 (hr) |
| JP (2) | JP7317375B2 (hr) |
| KR (1) | KR20200097690A (hr) |
| CN (2) | CN111182927B (hr) |
| AU (1) | AU2018382479A1 (hr) |
| BR (1) | BR112020011727A2 (hr) |
| CA (1) | CA3078104A1 (hr) |
| CL (1) | CL2020001542A1 (hr) |
| CR (1) | CR20200241A (hr) |
| CU (1) | CU24677B1 (hr) |
| DK (1) | DK3723815T3 (hr) |
| EC (1) | ECSP20029142A (hr) |
| ES (1) | ES2914832T3 (hr) |
| HR (1) | HRP20220764T1 (hr) |
| HU (1) | HUE059083T2 (hr) |
| IL (2) | IL313103A (hr) |
| JO (1) | JOP20200135A1 (hr) |
| LT (1) | LT3723815T (hr) |
| MX (2) | MX2020005430A (hr) |
| PE (1) | PE20210456A1 (hr) |
| PL (1) | PL3723815T3 (hr) |
| PT (1) | PT3723815T (hr) |
| RS (1) | RS63279B1 (hr) |
| SG (1) | SG11202002965WA (hr) |
| SI (1) | SI3723815T1 (hr) |
| TN (1) | TN2020000072A1 (hr) |
| UA (1) | UA126413C2 (hr) |
| WO (1) | WO2019115547A1 (hr) |
| ZA (1) | ZA202003472B (hr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL313103A (en) | 2017-12-11 | 2024-07-01 | Univ Muenchen Tech | PSMA ligands for imaging and endoradiotherapy |
| DK3917626T3 (da) | 2019-01-30 | 2023-08-28 | Technische Univ Muenchen Klinikum Rechts Der Isar | Psma-bindende dualmodusradiotracer og terapeutika |
| JP2022537773A (ja) | 2019-06-21 | 2022-08-29 | プロビンシャル・ヘルス・サービシーズ・オーソリティ | 前立腺特異的膜抗原を標的とする放射性標識化合物 |
| CN112321673B (zh) * | 2020-11-04 | 2022-09-20 | 北京市肿瘤防治研究所 | 一种前列腺特异性膜抗原靶向抑制剂及应用和探针 |
| CN113354707A (zh) * | 2021-06-07 | 2021-09-07 | 苏州思萃同位素技术研究所有限公司 | 一种针对前列腺癌的三功能诊疗一体化药物前体的合成方法及其产品 |
| WO2023173074A2 (en) * | 2022-03-10 | 2023-09-14 | The Research Foundation For The State University Of New York | Immunostimulant-cytotoxic conjugate composition and methods for cancer treatment |
| CN115010629B (zh) * | 2022-06-07 | 2024-02-23 | 西南医科大学附属医院 | 前列腺特异性膜抗原抑制剂、其核素标记物及制法和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200716632A (en) | 2005-05-16 | 2007-05-01 | Gilead Sciences Inc | Integrase inhibitor compounds |
| DK2318366T3 (en) * | 2008-08-01 | 2017-08-21 | Univ Johns Hopkins | PSMA BINDING MATERIALS AND APPLICATIONS THEREOF |
| WO2010135431A2 (en) * | 2009-05-19 | 2010-11-25 | The Regents Of The University Of California | Compositions, devices, and methods related to prostate-specific membrane antigen |
| EP3495355A1 (en) * | 2013-10-18 | 2019-06-12 | Deutsches Krebsforschungszentrum | Labeled inhibitors of prostate specific membrane antigen (psma), their use as imaging agents and pharmaceutical agents for the treatment of prostate cancer |
| WO2015171792A1 (en) | 2014-05-06 | 2015-11-12 | The Johns Hopkins University | Metal/radiometal-labeled psma inhibitors for psma-targeted imaging and radiotherapy |
| US10688200B2 (en) | 2015-12-31 | 2020-06-23 | Five Eleven Pharma Inc. | Urea-based prostate specific membrane antigen (PSMA) inhibitors for imaging and therapy |
| PL3433238T3 (pl) * | 2016-03-22 | 2021-12-13 | The Johns Hopkins University | Środki o wysokim powinowactwie ukierunkowane na antygen błonowy specyficzny dla gruczołu krokowego do endoradioterapii raka gruczołu krokowego |
| TW201930265A (zh) | 2017-12-11 | 2019-08-01 | 西班牙商阿爾米雷爾有限公司 | 作為acc抑制劑的吡咯衍生物 |
| SI3724176T1 (sl) | 2017-12-11 | 2022-04-29 | Helsinn Healthcare Sa | Fumaratna sol (R)-3-(1-(2,3-dikloro-4-(pirazin-2-il)fenil)-2,2,2-trifluoroetil)-1 -metil-1-(1-metilpiperidin-4-il) sečnine, postopki priprave in uporabe le-te |
| IL313103A (en) | 2017-12-11 | 2024-07-01 | Univ Muenchen Tech | PSMA ligands for imaging and endoradiotherapy |
-
2018
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2020
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2022
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2023
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