HRP20161315T1 - Postupak za proizvodnju degareliksa i njegovih međuprodukata - Google Patents
Postupak za proizvodnju degareliksa i njegovih međuprodukata Download PDFInfo
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- HRP20161315T1 HRP20161315T1 HRP20161315TT HRP20161315T HRP20161315T1 HR P20161315 T1 HRP20161315 T1 HR P20161315T1 HR P20161315T T HRP20161315T T HR P20161315TT HR P20161315 T HRP20161315 T HR P20161315T HR P20161315 T1 HRP20161315 T1 HR P20161315T1
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- Prior art keywords
- protecting group
- amino protecting
- hydrogen
- formula
- hydrogenation
- Prior art date
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- 238000000034 method Methods 0.000 title claims 16
- 108010052004 acetyl-2-naphthylalanyl-3-chlorophenylalanyl-1-oxohexadecyl-seryl-4-aminophenylalanyl(hydroorotyl)-4-aminophenylalanyl(carbamoyl)-leucyl-ILys-prolyl-alaninamide Proteins 0.000 title claims 3
- MEUCPCLKGZSHTA-XYAYPHGZSA-N degarelix Chemical compound C([C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CC=1C=CC(NC(=O)[C@H]2NC(=O)NC(=O)C2)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(NC(N)=O)C=C1 MEUCPCLKGZSHTA-XYAYPHGZSA-N 0.000 title claims 3
- 229960002272 degarelix Drugs 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 239000000543 intermediate Substances 0.000 title 1
- 125000006239 protecting group Chemical group 0.000 claims 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 108090000765 processed proteins & peptides Proteins 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 238000005984 hydrogenation reaction Methods 0.000 claims 6
- 229920001184 polypeptide Polymers 0.000 claims 6
- 102000004196 processed proteins & peptides Human genes 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 3
- DFZVZEMNPGABKO-SSDOTTSWSA-N (2r)-2-amino-3-pyridin-3-ylpropanoic acid Chemical compound OC(=O)[C@H](N)CC1=CC=CN=C1 DFZVZEMNPGABKO-SSDOTTSWSA-N 0.000 claims 2
- JPZXHKDZASGCLU-GFCCVEGCSA-N 3-(2-Naphthyl)-D-Alanine Chemical compound C1=CC=CC2=CC(C[C@@H](N)C(O)=O)=CC=C21 JPZXHKDZASGCLU-GFCCVEGCSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 210000004899 c-terminal region Anatomy 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
- C07K1/023—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution using racemisation inhibiting agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
- C07K1/026—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution by fragment condensation in solution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/08—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using activating agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/10—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using coupling agents
-
- 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
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/081—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
-
- 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
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- 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
- C07K5/08—Tripeptides
- C07K5/0815—Tripeptides with the first amino acid being basic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/23—Luteinising hormone-releasing hormone [LHRH]; Related peptides
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- 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Analytical Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Endocrinology (AREA)
- Peptides Or Proteins (AREA)
- Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (11)
1. Postupak za proizvodnju tekuće faze dekapeptida predstavljenog formulom (II)
(P1)AA1-AA2-AA3-AA4(P4)-AA5-AA6(P6)-AA7-AA8(P8)-AA9-AA10-NH2(II)
gdje je AA1 D-2Nal, AA2 je D-4Cpa, AA3 je D-3Pal, AA4 je Ser, AA5 je 4Aph(L-Hor), AA6 je D-Aph(Cbm), AA7 je Leu, AA8 je Lys(iPr), AA9 je Pro, AA10 je D-Ala;
P1 je amino zaštitna grupa ili acetil;
P4 je vodik ili hidroksilna zaštitna grupa, poželjno hidroksilna zaštitna grupa;
P6 je vodik ili amino zaštitna grupa; poželjno amino zaštitna grupa; i P8 je amino zaštitna grupa,
ili njegove farmaceutski prihvatljive sol ili solvata, koji obuhvaća korak udruživanja prvog polipeptida predstavljenog formulom (III)
(P1)AA1-AA2-AA3(III)
ili njegove soli, s drugim polipeptidom predstavljenim formulom (IV)
AA4(P4)-AA5-AA6(P6)-AA7-AA8(P8)-AA9-AA10-NH2(IV)
ili njegove soli, u tekućem reakcijskom mediju u prisutnosti reagensa koji veže peptide.
2. Postupak iz patentnog zahtjeva 1, pri čemu je P1 acetil; P4 je hidroksilna zaštitna grupa; P6 je vodik ili amino zaštitna grupa; i P8 je amino zaštitna grupa.
3. Tekući postupak za pripravu degareliksa obuhvaća postupak u skladu s patentnim zahtjevom 1 ili 2, koji slijedi postupak koji obuhvaća korak podvrgavanja dekapeptida predstavljenog formulom II ili njegove soli ili solvata tretiranju agensom za cijepanje zbog uklanjanja zaštitnih grupa P4, P6 i P8.
4. Postupak u skladu s patentnim zahtjevima 1, 2 ili 3, pri čemu je P1 acetil; P4 je tBut, a P8 je Boc.
5. Postupak za pripravu polipeptida predstavljen formulom (IV)
(P4)-AA4-AA5-AA6(P6)-AA7-AA8(P8)-AA9-AA10-NH2(IV)
gdje je
P4 vodik ili hidroksilna zaštitna grupa, poželjno hidroksilna zaštitna grupa;
P6 je vodik ili amino zaštitna grupa; poželjno amino zaštitna grupa; i
P8 je amino zaštitna grupa,
vezanjem polipeptida predstavljenog formulom (V) ili njegove soli ili solvata, s polipeptidom predstavljenim formulom (VI), ili njegovom soli ili solvatom,
(PN)AA4(P4)-AA5-AA6(P6)-AA7 (V)
AA8-(P8)-AA9-AA10-NH2 (VI)
i zatim uklanjanjem deprotekcijske grupe PN, pri čemu su AA4 do AA10, P4, P6 i P8 isti kao u patentnom zahtjevu 1, a PN je zaštitna grupa koja se može ukloniti hidrogenacijom.
6. Postupak u skladu s patentnim zahtjevom 5 pri čemu je PN benziloksikarbonil koji se uklanja hidrogenacijom tvari
(PN)AA4(P4)-AA5-AA6(P6)-AA7-AA8(P8)-AA9-AA10-NH2
u prisutnosti Pd/C katalizatora.
7. Postupak iz bilo kojeg od patentnih zahtjeva 5 ili 6, kojeg slijedi postupak iz bilo kojeg od patentnih zahtjeva 1 do 3.
8. Postupak za proizvodnju tvari
(PN)AA4(P4)-AA5-AA6(P6)-AA7
pri čemu su AA4 do AA7, P4 i P6 isti kao u patentnom zahtjevu 1, a PN je zaštitna grupa koja se može ukloniti hidrogenacijom, obuhvaća sljedeće korake:
(a) omogućavanje (PN2) AA5- AA6(P6)-AA7(PC), gdje P6 ima isto značenje kao i prethodno navedeno, (PN2) je N-terminalna amino zaštitna grupa ili vodik, a (PC) je C-terminalna karboksilna zaštitna grupa koja se može otcijepiti hidrogenacijom;
(b) uklanjanje amino zaštitne grupe (PN2), ako je prisutna;
(c) hidrogenacija H- AA5- AA6(P6)-AA7(PC) zbog dobivanja H- AA5- AA6(P6)-AA7; i
(d) reagiranje H- AA5- AA6(P6)-AA7 s aktiviranim esterom (PN)AA4(P4) zbog omogućavanja (PN)AA4(P4)-AA5-AA6(P6)-AA7, pri čemu AA4 ima isto značenje kao i prethodno navedeno, (P4) je hidroksilna zaštitna grupa ili vodik, a PN je zaštitna grupa koja se poželjno može ukloniti hidrogenacijom.
9. Postupak za pripravu otopine degareliksa, obuhvaća postupak iz patentnog zahtjeva 8, koji slijedi postupak iz bilo kojeg od patentnih zahtjeva 3 do 4.
10. Postupak iz jednog ili više od prethodnih patentnih zahtjeva, pri čemu se pH održava ispod 9, poželjno ispod 8.
11. Polipeptidne tvari predstavljene sljedećim formulama:
AA4(P4)AA5-AA6(P6)-AA7-AA8(P8)-AA9-AA10-NH2
(PN)AA4(P4)-AA5-AA6(P6)-AA7-AA8(P8)-AA9-AA10-NH2(PN)AA4(P4)-AA5-AA6(P6)-AA7
ili solima ili solvatima,
pri čemu je AA1 D-2Nal, AA2 je D-4Cpa, AA3 je D-3Pal, AA4 je Ser, AA5 je 4Aph(L-Hor), AA6 je D-Aph(Cbm), AA7 je Leu, AA8 je Lys(iPr), AA9 je Pro, AA10 je D-Ala;
P1 je amino zaštitna grupa ili acetil;
P4 je vodik ili hidroksilna zaštitna grupa, poželjno hidroksilna zaštitna grupa;
P6 je vodik ili amino zaštitna grupa; poželjno amino zaštitna grupa; i
P8 je amino zaštitna grupa, i PN je zaštitna grupa.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10189032A EP2447276A1 (en) | 2010-10-27 | 2010-10-27 | Process for the manufacture of Degarelix and its intermediates |
EP11776745.9A EP2632935B1 (en) | 2010-10-27 | 2011-10-26 | Process for the manufacture of degarelix and its intermediates |
PCT/EP2011/068735 WO2012055905A1 (en) | 2010-10-27 | 2011-10-26 | Process for the manufacture of degarelix and its intermediates |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20161315T1 true HRP20161315T1 (hr) | 2016-12-02 |
Family
ID=43531147
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20161315TT HRP20161315T1 (hr) | 2010-10-27 | 2016-10-11 | Postupak za proizvodnju degareliksa i njegovih međuprodukata |
Country Status (26)
Country | Link |
---|---|
US (2) | US9090656B2 (hr) |
EP (2) | EP2447276A1 (hr) |
JP (1) | JP6007187B2 (hr) |
KR (1) | KR101904808B1 (hr) |
CN (1) | CN103180335B (hr) |
AU (1) | AU2011322618B2 (hr) |
BR (1) | BR112013010360B1 (hr) |
CA (1) | CA2815270A1 (hr) |
DK (1) | DK2632935T3 (hr) |
ES (1) | ES2606753T3 (hr) |
HR (1) | HRP20161315T1 (hr) |
HU (1) | HUE030184T2 (hr) |
IL (1) | IL225687A (hr) |
JO (1) | JO3243B1 (hr) |
LT (1) | LT2632935T (hr) |
MX (1) | MX343058B (hr) |
NZ (1) | NZ609064A (hr) |
PL (1) | PL2632935T3 (hr) |
PT (1) | PT2632935T (hr) |
RS (1) | RS55193B1 (hr) |
RU (1) | RU2602042C2 (hr) |
SA (1) | SA111320880B1 (hr) |
SI (1) | SI2632935T1 (hr) |
TW (1) | TWI515201B (hr) |
WO (1) | WO2012055905A1 (hr) |
ZA (1) | ZA201302670B (hr) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
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GB0117057D0 (en) * | 2001-07-12 | 2001-09-05 | Ferring Bv | Pharmaceutical composition |
JOP20090061B1 (ar) | 2008-02-11 | 2021-08-17 | Ferring Int Center Sa | طريقة معالجة سرطان البروستاتا بمضادات الهرمونات التناسلية GnRH |
CN105663059A (zh) * | 2009-05-01 | 2016-06-15 | 辉凌公司 | 用于治疗前列腺癌的组合物 |
US20110039787A1 (en) * | 2009-07-06 | 2011-02-17 | Ferring International Center S.A. | Compositions, kits and methods for treating benign prostate hyperplasia |
EP2632934B1 (en) | 2010-10-27 | 2016-11-30 | Ferring B.V. | Process for the manufacture of degarelix and its intermediates |
EP2447276A1 (en) | 2010-10-27 | 2012-05-02 | Ferring B.V. | Process for the manufacture of Degarelix and its intermediates |
JO3755B1 (ar) | 2011-01-26 | 2021-01-31 | Ferring Bv | تركيبات تستوستيرون |
TWI580443B (zh) | 2012-06-01 | 2017-05-01 | 菲瑞茵公司 | 地蓋瑞利(degarelix)之製備技術 |
CN103992378A (zh) * | 2013-11-01 | 2014-08-20 | 杭州诺泰制药技术有限公司 | 一种制备醋酸地加瑞克的方法 |
CN106589071B (zh) * | 2016-12-12 | 2020-09-08 | 江苏诺泰澳赛诺生物制药股份有限公司 | 一种地加瑞克的合成方法 |
CN109748954B (zh) * | 2017-11-06 | 2022-03-01 | 正大天晴药业集团股份有限公司 | 一种地加瑞克的纯化方法 |
CN107955061B (zh) * | 2017-11-15 | 2021-07-30 | 连云港恒运药业有限公司 | 地加瑞克关键中间体的制备方法 |
CN109929007B (zh) * | 2017-12-15 | 2023-07-28 | 连云港恒运药业有限公司 | 地加瑞克关键二肽中间体的制备方法 |
CN110330552B (zh) * | 2019-08-14 | 2021-03-16 | 凯莱英生命科学技术(天津)有限公司 | 醋酸地加瑞克的合成方法 |
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