ZA200108335B - Method for producing cyclo-(Asp-DPhe-NMeVal-Arg-Gly). - Google Patents
Method for producing cyclo-(Asp-DPhe-NMeVal-Arg-Gly). Download PDFInfo
- Publication number
- ZA200108335B ZA200108335B ZA200108335A ZA200108335A ZA200108335B ZA 200108335 B ZA200108335 B ZA 200108335B ZA 200108335 A ZA200108335 A ZA 200108335A ZA 200108335 A ZA200108335 A ZA 200108335A ZA 200108335 B ZA200108335 B ZA 200108335B
- Authority
- ZA
- South Africa
- Prior art keywords
- nmeval
- dphe
- asp
- gly
- arg
- Prior art date
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- PAFZNILMFXTMIY-UHFFFAOYSA-O cyclohexylammonium Chemical class [NH3+]C1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-O 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- RMGVZKRVHHSUIM-UHFFFAOYSA-N dithionic acid Chemical compound OS(=O)(=O)S(O)(=O)=O RMGVZKRVHHSUIM-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- LLYKPZOWCPVRPD-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine;n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=CC=N1 LLYKPZOWCPVRPD-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000013930 proline Nutrition 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
- C07K5/06086—Dipeptides with the first amino acid being basic
- C07K5/06095—Arg-amino acid
-
- 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
- C07K5/0819—Tripeptides with the first amino acid being acidic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
-
- 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)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19910727 | 1999-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200108335B true ZA200108335B (en) | 2003-01-10 |
Family
ID=7900511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200108335A ZA200108335B (en) | 1999-03-11 | 2001-10-10 | Method for producing cyclo-(Asp-DPhe-NMeVal-Arg-Gly). |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US6822074B1 (no) |
| EP (1) | EP1159296B1 (no) |
| JP (1) | JP4762418B2 (no) |
| KR (1) | KR100645002B1 (no) |
| CN (1) | CN1200947C (no) |
| AR (1) | AR022905A1 (no) |
| AT (1) | ATE267839T1 (no) |
| AU (1) | AU762540B2 (no) |
| BR (1) | BR0008863A (no) |
| CA (1) | CA2366694C (no) |
| CZ (1) | CZ299879B6 (no) |
| DE (1) | DE50006598D1 (no) |
| DK (1) | DK1159296T3 (no) |
| ES (1) | ES2221616T3 (no) |
| HK (1) | HK1044780B (no) |
| HU (1) | HUP0200369A3 (no) |
| ID (1) | ID30126A (no) |
| MY (1) | MY120083A (no) |
| NO (1) | NO330030B1 (no) |
| PL (1) | PL202996B1 (no) |
| PT (1) | PT1159296E (no) |
| RU (1) | RU2243974C2 (no) |
| SE (1) | SE1159296T5 (no) |
| SK (1) | SK285387B6 (no) |
| TW (1) | TWI269798B (no) |
| UA (1) | UA71608C2 (no) |
| WO (1) | WO2000053627A1 (no) |
| ZA (1) | ZA200108335B (no) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0814519D0 (en) | 2008-08-08 | 2008-09-17 | Imp Innovations Ltd | Process |
| EP2430162A4 (en) * | 2009-05-15 | 2013-04-24 | Ca Nat Research Council | DNA SEQUENCES AND METHOD OF PROCESSING ENCODING CARYOPHYLLACEAE AND CARYOPHYLLACEAE-SIMILAR CYCLOPEPTIDE TREATMENTS |
| KR20120060947A (ko) * | 2009-05-20 | 2012-06-12 | 메르크 파텐트 게엠베하 | 신규 고체 물질 ｛［（2ｓ,5ｒ,8ｓ,11ｓ）-5-벤질-11-（3-구아니디노-프로필）-8-이소프로필-7-메틸-3,6,9,12,15-펜타옥소-1,4,7,10,13-펜타아자-시클로펜타데크-2-일］-아세트산｝ 및 이의 제조 방법 |
| KR20120104316A (ko) | 2009-12-10 | 2012-09-20 | 메르크 파텐트 게엠베하 | 올리고펩티드, 바람직하게는 실렌기티드를 포함하는 약학 조성물 |
| CA2838573A1 (en) | 2011-06-09 | 2012-12-13 | Simon Goodman | Treatment of cancers and metastases with suspensions of cilengitide in carrier |
| US11753440B2 (en) * | 2018-06-05 | 2023-09-12 | Dsm Ip Assets B.V. | Methods for the synthesis of arginine-containing peptides |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1038741B (de) * | 1956-09-14 | 1958-09-11 | Eberhard Brecklinghaus | Aus Gummi oder einem anderen elastischen Werkstoff bestehender Kantenschoner fuer Treppenstufen aus Beton od. dgl. |
| US3630660A (en) * | 1968-10-31 | 1971-12-28 | Burlington Industries Inc | Process for removal of moisture and/or solvents from textile materials |
| UA43823C2 (uk) * | 1992-07-06 | 2002-01-15 | Мерк Патент Геселлшафт Міт Бесшренктер Хафтунг | ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ ДЛЯ ІНГІБУВАННЯ ІНТЕГРИН <font face="Symbol">a</font><sub>V</sub><font face="Symbol">b</font><sub>3</sub>-ОПОСЕРЕДКОВАНОЇ КЛІТИННОЇ АДГЕЗІЇ КЛІТИН ССАВЦІВ, СПОСІБ ЛІКУВАННЯ ТА ПРОФІЛАКТИКИ ЗАХВОРЮВАННЯ, АСОЦІЙОВАНОГО З ПОРУШЕННЯМ АДГЕЗІЇ КЛІТИН, СПОСІБ БЛОКУВАННЯ ЗВ'ЯЗУВАННЯ ФІБРИНОГЕНОМ ІНТЕГРИНУ, КОМПОЗИЦІЯ ДЛЯ ЗАГОЄННЯ РАН |
| JPH06263798A (ja) * | 1993-01-13 | 1994-09-20 | Takeda Chem Ind Ltd | βターン及びγターンを有する環状ペンタペプチド、その製造方法および用途 |
| EP0606881B1 (en) * | 1993-01-13 | 1999-05-12 | Takeda Chemical Industries, Ltd. | Cyclic pentapeptides having a beta-turn and a gamma-turn |
| DE4310643A1 (de) * | 1993-04-01 | 1994-10-06 | Merck Patent Gmbh | Cyclische Adhäsionsinhibitoren |
| ES2188665T3 (es) * | 1994-06-02 | 2003-07-01 | Forssmann Wolf Georg | Procedimiento para la preparacion de fragmentos de cardiodilatina, fragmentos de cardiodilatina muy purificados y productos intermedios para su preparacion. |
| DE19534177A1 (de) * | 1995-09-15 | 1997-03-20 | Merck Patent Gmbh | Cyclische Adhäsionsinhibitoren |
| DE19538741A1 (de) | 1995-10-18 | 1997-04-24 | Merck Patent Gmbh | Cyclopeptidderivate |
| DE19613933A1 (de) | 1996-04-06 | 1997-10-09 | Merck Patent Gmbh | Cyclische Adhäsionsinhibitoren |
| PL330240A1 (en) * | 1996-05-31 | 1999-05-10 | Scripps Research Inst | Methods and compositions useful in inhibiting angiogenesis in which alphavbeta5 acts as intermediary |
| DE19728524A1 (de) * | 1997-07-04 | 1999-01-07 | Merck Patent Gmbh | Cyclische Azapeptide |
-
2000
- 2000-01-03 UA UA2001106897A patent/UA71608C2/uk unknown
- 2000-03-01 PL PL349646A patent/PL202996B1/pl not_active IP Right Cessation
- 2000-03-01 BR BR0008863-3A patent/BR0008863A/pt active Search and Examination
- 2000-03-01 US US09/936,230 patent/US6822074B1/en not_active Expired - Fee Related
- 2000-03-01 RU RU2001126541/04A patent/RU2243974C2/ru not_active IP Right Cessation
- 2000-03-01 SE SE00820481T patent/SE1159296T5/xx unknown
- 2000-03-01 WO PCT/EP2000/001751 patent/WO2000053627A1/de active IP Right Grant
- 2000-03-01 EP EP00920461A patent/EP1159296B1/de not_active Expired - Lifetime
- 2000-03-01 MY MYPI20000799A patent/MY120083A/en unknown
- 2000-03-01 PT PT00920461T patent/PT1159296E/pt unknown
- 2000-03-01 JP JP2000604062A patent/JP4762418B2/ja not_active Expired - Fee Related
- 2000-03-01 DK DK00920461T patent/DK1159296T3/da active
- 2000-03-01 KR KR1020017011291A patent/KR100645002B1/ko not_active IP Right Cessation
- 2000-03-01 CA CA2366694A patent/CA2366694C/en not_active Expired - Fee Related
- 2000-03-01 HU HU0200369A patent/HUP0200369A3/hu unknown
- 2000-03-01 SK SK1255-2001A patent/SK285387B6/sk not_active IP Right Cessation
- 2000-03-01 CZ CZ20013214A patent/CZ299879B6/cs not_active IP Right Cessation
- 2000-03-01 DE DE50006598T patent/DE50006598D1/de not_active Expired - Lifetime
- 2000-03-01 ID IDW00200102095A patent/ID30126A/id unknown
- 2000-03-01 ES ES00920461T patent/ES2221616T3/es not_active Expired - Lifetime
- 2000-03-01 CN CNB008048746A patent/CN1200947C/zh not_active Expired - Fee Related
- 2000-03-01 AT AT00920461T patent/ATE267839T1/de active
- 2000-03-01 AU AU41034/00A patent/AU762540B2/en not_active Ceased
- 2000-03-07 TW TW089104103A patent/TWI269798B/zh not_active IP Right Cessation
- 2000-03-10 AR ARP000101079A patent/AR022905A1/es active IP Right Grant
-
2001
- 2001-09-10 NO NO20014383A patent/NO330030B1/no not_active IP Right Cessation
- 2001-10-10 ZA ZA200108335A patent/ZA200108335B/en unknown
-
2002
- 2002-08-29 HK HK02106365.2A patent/HK1044780B/zh not_active IP Right Cessation
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