HRP20191443T1 - Antitumorska sjedinjenja - Google Patents
Antitumorska sjedinjenja Download PDFInfo
- Publication number
- HRP20191443T1 HRP20191443T1 HRP20191443T HRP20191443T1 HR P20191443 T1 HRP20191443 T1 HR P20191443T1 HR P20191443 T HRP20191443 T HR P20191443T HR P20191443 T1 HRP20191443 T1 HR P20191443T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- cancer
- formula
- pharmaceutically acceptable
- lung cancer
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 21
- 230000000259 anti-tumor effect Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims 9
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 206010009944 Colon cancer Diseases 0.000 claims 5
- 239000002552 dosage form Substances 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 206010006187 Breast cancer Diseases 0.000 claims 3
- 208000026310 Breast neoplasm Diseases 0.000 claims 3
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 3
- 206010041067 Small cell lung cancer Diseases 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 201000005202 lung cancer Diseases 0.000 claims 3
- 208000020816 lung neoplasm Diseases 0.000 claims 3
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 3
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 3
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 206010039491 Sarcoma Diseases 0.000 claims 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000000284 extract Substances 0.000 claims 2
- 206010017758 gastric cancer Diseases 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 201000011549 stomach cancer Diseases 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 229940049920 malate Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D515/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D515/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4995—Pyrazines or piperazines forming part of bridged ring systems
-
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (15)
1. Sjedinjenje sa formulom V, ili njegova farmaceutski prihvatljiva sol ili estar:
2. Sjedinjenje sa formulom VI, ili njegova farmaceutski prihvatljiva sol ili estar:
3. Sjedinjenje u skladu sa patentnim zahtjevom 1 ili patentnim zahtjevom 2, gdje je sol odabrana od hidroklorid, hidrobromid, hidrojodid, sulfat, nitrat, fosfat, acetat, trifluoroacetat, maleat, fumarat, citrat, oksalat, sukcinat, tartarat, malat, mandelat, metansulfonat, p-toluensulfonat; natrij, kalij, kalcij, amonij soli; i soli etilendiamina, etanolamina, N,N-dial kilen etanolamina, trietanolamina i baznih aminokiselina.
4. Farmaceutska kompozicija koja sadrži sjedinjenje u skladu sa bilo kojim od patentnih zahtjeva 1 do 3 ili njegovu farmaceutski prihvatljivu sol ili estar i farmaceutski prihvatljiv nosač.
5. Dozni oblik koji obuhvaća farmaceutsku kompoziciju u skladu sa patentnim zahtjevom 4.
6. Sjedinjenje u skladu sa bilo kojim od patentnih zahtjeva 1 do 3 ili njegova farmaceutski prihvatljiva sol ili estar, kompozicija u skladu sa patentnim zahtjevom 4 ili dozni oblik u skladu sa patentnim zahtjevom 5, za primjenu kao lijek.
7. Sjedinjenje u skladu sa bilo kojim od patentnih zahtjeva 1 do 3 ili njegova farmaceutski prihvatljiva sol ili estar, kompozicija u skladu sa patentnim zahtjevom 4 ili dozni oblik u skladu sa patentni zahtjevom 5, za primjenu u liječenju raka.
8. Sjedinjenje, kompozicija ili dozni oblik u skladu sa patentnim zahtjevom 7, gdje je rak odabran od raka pluća uključujući rak pluća malih stanica i rak pluća nemalih stanica, rak debelog crijeva, kolorektalnog raka, raka dojke, raka gušterače, sarkoma, raka jajnika i raka želuca.
9. Sjedinjenje, kompozicija ili dozni oblik u skladu sa patentnim zahtjevom 8, gdje je rak odabran od raka pluća uključujući rak pluća malih stanica i rak pluća nemalih stanica, raka dojke, raka gušterače i kolorektalnog raka.
10. Proces za dobivanje sjedinjenja sa formulom V kao što je definirano u patentnom zahtjevu 1 ili njegove farmaceutski prihvatljive soli ili ekstrakti:
koji obuhvaćaju korak reagiranja sjedinjenja sa formulom II sa sjedinjenjem sa formulom III da se dobije sjedinjenje sa formulom IV:
gdje:
X je -O-;
R2 je acetil;
R3 je vodik;
R4 je -CH2OH.
11. Proces u skladu sa patentnim zahtjevom 10, koji obuhvata dalji korak zamjene cijano grupe u sjedinjenju sa formulom IV sa hidroksi grupom da se dobije sjedinjenje sa formulom V.
12. Proces za dobivanje sjedinjenja sa formulom VI kao što je definirano u patentnom zahtjevu 2 ili njegove farmaceutski prihvatljive soli ili ekstrakta:
koji obuhvata korak reagiranja sjedinjenja sa formulom II sa sjedinjenjem sa formulom III da se dobije sjedinjenje sa formulom IV:
gdje:
X je -O-;
R2 je acetil;
R3 je vodik;
R4 je vodik.
13. Proces u skladu sa patentnim zahtjevom 12, koji obuhvata dalji korak zamjene cijano grupe u sjedinjenju sa formulom IV sa hidroksi grupom da se dobije sjedinjenje sa formulom VI.
14. Komplet koji sadrži terapijski efikasnu količinu sjedinjenja u skladu sa bilo kojim od patentnih zahtjeva 1 do 3 i farmaceutski prihvatljiv nosač.
15. Komplet u skladu sa patentnim zahtjevom 14 koji dalje sadrži uputstva za primjenu sjedinjenja u liječenju raka, i poželjnije raka odabranog od raka pluća, uključujući rak pluća nemalih stanica i rak pluća malih stanica, raka debelog crijeva, kolorektalnog raka, raka dojke, raka gušterače, sarkoma, raka jajnika i raka želuca.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP17382228 | 2017-04-27 | ||
EP17382497 | 2017-07-26 | ||
EP18382287.3A EP3395820B1 (en) | 2017-04-27 | 2018-04-27 | Antitumoral compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20191443T1 true HRP20191443T1 (hr) | 2019-11-15 |
Family
ID=62063080
Family Applications (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20230455TT HRP20230455T1 (hr) | 2017-04-27 | 2018-04-27 | Antitumorski spojevi |
HRP20231233TT HRP20231233T1 (hr) | 2017-04-27 | 2018-04-27 | Antitumorski spojevi |
HRP20230433TT HRP20230433T1 (hr) | 2017-04-27 | 2018-04-27 | Antitumorski spojevi |
HRP20191442 HRP20191442T1 (hr) | 2017-04-27 | 2019-08-09 | Antitumorska sjedinjenja |
HRP20191443 HRP20191443T1 (hr) | 2017-04-27 | 2019-08-09 | Antitumorska sjedinjenja |
Family Applications Before (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20230455TT HRP20230455T1 (hr) | 2017-04-27 | 2018-04-27 | Antitumorski spojevi |
HRP20231233TT HRP20231233T1 (hr) | 2017-04-27 | 2018-04-27 | Antitumorski spojevi |
HRP20230433TT HRP20230433T1 (hr) | 2017-04-27 | 2018-04-27 | Antitumorski spojevi |
HRP20191442 HRP20191442T1 (hr) | 2017-04-27 | 2019-08-09 | Antitumorska sjedinjenja |
Country Status (38)
Country | Link |
---|---|
US (5) | US11332480B2 (hr) |
EP (5) | EP3395821B1 (hr) |
JP (5) | JP6501947B2 (hr) |
KR (3) | KR102492283B1 (hr) |
CN (4) | CN114736219B (hr) |
AU (4) | AU2018260314C1 (hr) |
BR (1) | BR112019022282A2 (hr) |
CA (1) | CA3061518A1 (hr) |
CL (1) | CL2019003057A1 (hr) |
CO (1) | CO2019011967A2 (hr) |
CY (3) | CY1121885T1 (hr) |
DK (5) | DK4101855T3 (hr) |
EC (1) | ECSP19083967A (hr) |
ES (5) | ES2944344T3 (hr) |
FI (3) | FI4101855T3 (hr) |
HK (2) | HK1255938B (hr) |
HR (5) | HRP20230455T1 (hr) |
HU (5) | HUE046109T2 (hr) |
IL (3) | IL289963B2 (hr) |
JO (1) | JOP20190254A1 (hr) |
LT (5) | LT4101855T (hr) |
MA (2) | MA44020B1 (hr) |
MD (5) | MD3395821T2 (hr) |
ME (2) | ME03467B (hr) |
MX (3) | MX392829B (hr) |
MY (1) | MY198004A (hr) |
PH (1) | PH12019550224A1 (hr) |
PL (5) | PL4101855T3 (hr) |
PT (2) | PT3395821T (hr) |
RS (5) | RS59173B1 (hr) |
SG (2) | SG11201909841RA (hr) |
SI (5) | SI3395820T1 (hr) |
SM (5) | SMT202300169T1 (hr) |
TN (2) | TN2019000211A1 (hr) |
TW (3) | TWI807411B (hr) |
UY (1) | UY37706A (hr) |
WO (1) | WO2018197663A1 (hr) |
ZA (1) | ZA201907119B (hr) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JOP20190254A1 (ar) * | 2017-04-27 | 2019-10-27 | Pharma Mar Sa | مركبات مضادة للأورام |
TWI824043B (zh) * | 2018-10-25 | 2023-12-01 | 西班牙商瑪製藥股份有限公司 | 藥物抗體共軛物 |
PH12022551216A1 (en) * | 2019-11-21 | 2023-07-17 | Pharma Mar Sa | Methods of treating small cell lung cancer with lurbinectedin formulations |
PE20230785A1 (es) * | 2020-04-21 | 2023-05-11 | Pharma Mar Sa | Conjugados de anticuerpos de farmacos |
TW202144369A (zh) * | 2020-04-26 | 2021-12-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 海鞘素類衍生物及其製備方法與醫藥用途 |
CN117295499A (zh) | 2021-05-19 | 2023-12-26 | 法马马有限公司 | 海鞘素的给药方案 |
WO2024186263A1 (en) * | 2023-03-07 | 2024-09-12 | Axcynsis Therapeutics Pte. Ltd. | Antibody-drug conjugates comprising trabectedin and lurbinectedin derivatives |
WO2025077996A1 (en) | 2023-10-09 | 2025-04-17 | Pharma Mar, S.A. | Synthetic process for the manufacture of ecteinascidin compounds |
EP4563149A1 (en) | 2023-11-30 | 2025-06-04 | Pharma Mar, S.A. | Lurbinectedin, ecubectedin and a related compound for use in the treatment of skin cancers |
Family Cites Families (220)
Publication number | Priority date | Publication date | Assignee | Title |
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US3205220A (en) | 1961-10-26 | 1965-09-07 | Lilly Co Eli | Leurosidine and leurocristine and their production |
US4762949A (en) | 1979-06-20 | 1988-08-09 | University Of Illinois Foundation | Acyl and carbamimidoyl alkanediamines |
GB2058047B (en) | 1979-07-11 | 1983-09-21 | Asahi Chemical Ind | Amides and amidines |
FR2461995A1 (fr) | 1979-07-20 | 1981-02-06 | Lcc Cice Cie Europ Compo Elect | Transducteur magneto-electrique pour systeme d'enregistrement magnetique, et systeme d'enregistrement comportant un tel transducteur |
US4782135A (en) | 1980-09-12 | 1988-11-01 | Board Of Trustees, University Of Illinois | Composition of matter and process |
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EP0048149B1 (en) | 1980-09-12 | 1983-11-30 | University of Illinois Foundation | Novel antibiotics, derivatives thereof, processes for their extraction, and compositions containing them |
US4950649A (en) | 1980-09-12 | 1990-08-21 | University Of Illinois | Didemnins and nordidemnins |
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IT1153974B (it) | 1982-09-23 | 1987-01-21 | Erba Farmitalia | Composizioni farmacologiche a base di cisplatino e metodo per il loro ottenimento |
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JPS59225189A (ja) | 1983-06-03 | 1984-12-18 | Shionogi & Co Ltd | キノナミン誘導体およびその製造法 |
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JPS6084288A (ja) | 1983-10-13 | 1985-05-13 | Shionogi & Co Ltd | シアノキノナミンアセテ−ト類およびその製造法 |
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