NL194729C - Werkwijze voor de bereiding van peptidealcoholen via vaste fase. - Google Patents
Werkwijze voor de bereiding van peptidealcoholen via vaste fase. Download PDFInfo
- Publication number
- NL194729C NL194729C NL8702345A NL8702345A NL194729C NL 194729 C NL194729 C NL 194729C NL 8702345 A NL8702345 A NL 8702345A NL 8702345 A NL8702345 A NL 8702345A NL 194729 C NL194729 C NL 194729C
- Authority
- NL
- Netherlands
- Prior art keywords
- group
- resin
- peptide
- groups
- alcohol
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims description 53
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 10
- 150000001298 alcohols Chemical class 0.000 title description 7
- 239000007790 solid phase Substances 0.000 title description 4
- 229920005989 resin Polymers 0.000 claims description 38
- 239000011347 resin Substances 0.000 claims description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 12
- 239000004793 Polystyrene Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229920003002 synthetic resin Polymers 0.000 claims description 5
- DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 claims description 4
- 108010016076 Octreotide Proteins 0.000 claims description 4
- 229960002700 octreotide Drugs 0.000 claims description 4
- 239000000057 synthetic resin Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 23
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 102000004196 processed proteins & peptides Human genes 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 235000001014 amino acid Nutrition 0.000 description 12
- 150000001413 amino acids Chemical class 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- -1 polyethylene Polymers 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000004036 acetal group Chemical group 0.000 description 6
- 125000003158 alcohol group Chemical group 0.000 description 6
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920001184 polypeptide Polymers 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- 150000001414 amino alcohols Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 125000006850 spacer group Chemical group 0.000 description 5
- MUVQIIBPDFTEKM-QWWZWVQMSA-N (2r,3r)-2-aminobutane-1,3-diol Chemical group C[C@@H](O)[C@H](N)CO MUVQIIBPDFTEKM-QWWZWVQMSA-N 0.000 description 4
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 4
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- OYNIIKHNXNPSAG-UHFFFAOYSA-N 2-(4-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C=O)C=C1 OYNIIKHNXNPSAG-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 229960002684 aminocaproic acid Drugs 0.000 description 2
- 238000004873 anchoring Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229920005990 polystyrene resin Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- HBDJFVFTHLOSDW-DNDLZOGFSA-N (2r,3r,4r,5r)-2,3,5,6-tetrahydroxy-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal;hydrate Chemical compound O.O=C[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HBDJFVFTHLOSDW-DNDLZOGFSA-N 0.000 description 1
- VVQIIIAZJXTLRE-QMMMGPOBSA-N (2s)-2-amino-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid Chemical compound CC(C)(C)OC(=O)NCCCC[C@H](N)C(O)=O VVQIIIAZJXTLRE-QMMMGPOBSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical group C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- VUCNQOPCYRJCGQ-UHFFFAOYSA-N 2-[4-(hydroxymethyl)phenoxy]acetic acid Chemical compound OCC1=CC=C(OCC(O)=O)C=C1 VUCNQOPCYRJCGQ-UHFFFAOYSA-N 0.000 description 1
- CFBPGADIXTVKBS-UHFFFAOYSA-N 2-amino-3-sulfanylpropan-1-ol Chemical group OCC(N)CS CFBPGADIXTVKBS-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical group OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- ZKDXHLFLKKWCBY-UHFFFAOYSA-N 4-Hydroxymethyl-3-methoxyphenoxyacetic acid Chemical compound COC1=CC(OCC(O)=O)=CC=C1CO ZKDXHLFLKKWCBY-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
- LLHRMWHYJGLIEV-UHFFFAOYSA-N desoxy Chemical group COC1=CC(CCN)=CC(OC)=C1C LLHRMWHYJGLIEV-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000000373 fatty alcohol group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- AUNMDDDYIVMYNS-QWWZWVQMSA-N n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-2,2,2-trifluoroacetamide Chemical compound C[C@@H](O)[C@@H](CO)NC(=O)C(F)(F)F AUNMDDDYIVMYNS-QWWZWVQMSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical class C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 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
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- 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
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
- C07K1/1072—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups
- C07K1/1077—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Analytical Chemistry (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3634797 | 1986-10-13 | ||
| DE3634825 | 1986-10-13 | ||
| DE3634825 | 1986-10-13 | ||
| DE3634797 | 1986-10-13 | ||
| DE3634826 | 1986-10-13 | ||
| DE3634826 | 1986-10-13 | ||
| DE3712626 | 1987-04-14 | ||
| DE3712626 | 1987-04-14 | ||
| CH315387 | 1987-08-17 | ||
| CH315387 | 1987-08-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NL8702345A NL8702345A (nl) | 1988-05-02 |
| NL194729B NL194729B (nl) | 2002-09-02 |
| NL194729C true NL194729C (nl) | 2003-01-07 |
Family
ID=27509117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8702345A NL194729C (nl) | 1986-10-13 | 1987-10-01 | Werkwijze voor de bereiding van peptidealcoholen via vaste fase. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5656721A (OSRAM) |
| JP (2) | JPH0645639B2 (OSRAM) |
| KR (1) | KR960016861B1 (OSRAM) |
| AU (2) | AU617986B2 (OSRAM) |
| BE (1) | BE1003752A4 (OSRAM) |
| CA (1) | CA1340985C (OSRAM) |
| CH (2) | CH682632A5 (OSRAM) |
| DE (1) | DE3790635T1 (OSRAM) |
| DK (1) | DK174337B1 (OSRAM) |
| ES (1) | ES2007418A6 (OSRAM) |
| FI (1) | FI874495A7 (OSRAM) |
| FR (1) | FR2609991A1 (OSRAM) |
| GB (2) | GB2199829B (OSRAM) |
| GR (1) | GR871567B (OSRAM) |
| HU (3) | HU906340D0 (OSRAM) |
| IE (1) | IE912442A1 (OSRAM) |
| LU (1) | LU87014A1 (OSRAM) |
| NL (1) | NL194729C (OSRAM) |
| NZ (1) | NZ222133A (OSRAM) |
| PL (1) | PL157156B1 (OSRAM) |
| PT (1) | PT85904B (OSRAM) |
| SE (2) | SE8703938L (OSRAM) |
| WO (1) | WO1988002756A2 (OSRAM) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU906340D0 (en) * | 1986-10-13 | 1991-04-29 | Sandoz Ag | Synthesis in solid phase for producing peptonic alcohols |
| DE3845000C2 (de) * | 1987-07-10 | 1998-11-19 | Novartis Ag | Anwendung von Octreotid zur Behandlung von Brustkrebs |
| JPH03502328A (ja) * | 1988-02-01 | 1991-05-30 | ジ・アップジョン・カンパニー | 極性末端基類を有するレニン抑制ペプチド類 |
| GB2218102B (en) * | 1988-04-08 | 1992-09-16 | Sandoz Ltd | Calcitonin peptide derivatives |
| DE3910667A1 (de) * | 1988-04-11 | 1989-10-19 | Sandoz Ag | Peptidderivate |
| GB8813339D0 (en) * | 1988-06-06 | 1988-07-13 | Sandoz Ltd | Improvements in/relating to organic compounds |
| FR2638968B1 (fr) * | 1988-11-11 | 1994-10-07 | Sandoz Sa | Nouvelle utilisation therapeutique de la somatostatine et de ses analogues et derives |
| US5753627A (en) * | 1988-12-05 | 1998-05-19 | Novartis Ag | Use of certain complexed somatostatin peptides for the invivo imaging of somatostatin receptor-positive tumors and metastasis |
| MY106120A (en) * | 1988-12-05 | 1995-03-31 | Novartis Ag | Peptide derivatives. |
| US5776894A (en) * | 1988-12-05 | 1998-07-07 | Novartis Ag | Chelated somatostatin peptides and complexes thereof, pharmaceutical compositions containing them and their use in treating tumors |
| IT1229514B (it) * | 1989-01-30 | 1991-09-03 | Farmhispania S A A Montme | Glicoconiugati anfifilici sintetici per impiego neurologico. |
| DK111489D0 (da) * | 1989-03-08 | 1989-03-08 | Novo Nordisk As | Peptider |
| DE4206858A1 (de) * | 1992-03-05 | 1993-09-09 | Behringwerke Ag | Glycopeptid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische mittel |
| IT1260156B (it) * | 1992-08-03 | 1996-03-28 | Fidia Spa | Derivati dell'acido neuraminico |
| TW263437B (OSRAM) * | 1992-09-24 | 1995-11-21 | Takeda Pharm Industry Co Ltd | |
| US5710244A (en) * | 1992-12-31 | 1998-01-20 | Labroo; Virender M. | Derivatized calcitonins |
| US5508387A (en) * | 1993-08-04 | 1996-04-16 | Glycomed Incorporated | Selectin binding glycopeptides |
| DE69432758T2 (de) | 1993-08-09 | 2004-02-19 | Société de Conseils de Recherches et d'Applications Scientifiques S.A.S. | Therapeutisch wirksame peptidderivate |
| US5632969A (en) * | 1994-10-13 | 1997-05-27 | Merck & Co., Inc. | N3 S2 chelating ligands optionally radiolabelled with Tc or Re, useful for diagnostic or therapeutic applications |
| US5556939A (en) * | 1994-10-13 | 1996-09-17 | Merck Frosst Canada, Inc. | TC or RE radionuclide labelled chelate, hexapeptide complexes useful for diagnostic or therapeutic applications |
| JP3896430B2 (ja) * | 1996-07-15 | 2007-03-22 | アークレイ株式会社 | 糖化アミノ化合物の製造方法 |
| IL119029A0 (en) | 1996-08-07 | 1996-11-14 | Yeda Res & Dev | Long-acting drugs and pharamaceutical compositions comprising them |
| US6004928A (en) * | 1997-05-13 | 1999-12-21 | Biomeasure, Incorporated | Method of treating hyperlipidemia |
| WO1998051330A1 (en) | 1997-05-13 | 1998-11-19 | Societe De Conseils De Recherches Et D'applications Scientifiques S.A. (S.C.R.A.S.) | Method and compositions for treating hyperlipidemia and other conditions |
| ES2202864T3 (es) | 1997-05-13 | 2004-04-01 | Societe De Conseils De Recherches Et D'applications Scientifiques S.A.S. | Agonistas de la somatostatina para disminuir el peso corporal. |
| JP4372345B2 (ja) * | 1998-02-13 | 2009-11-25 | アミリン・ファーマシューティカルズ，インコーポレイテッド | 新規な混合アミリン活性化合物 |
| US5968903A (en) * | 1998-05-07 | 1999-10-19 | Biomeasure, Incorporated | Inhibition of H. pylori proliferation |
| US20050037490A1 (en) * | 1999-10-29 | 2005-02-17 | Lawrence Rosenberg | Medium for preparing dedifferentiated cells |
| EP1381396B1 (en) * | 2001-04-23 | 2009-04-01 | Mallinckrodt Inc. | Tc and re labeled radioactive glycosylated octreotide derivatives |
| ATE424414T1 (de) | 2001-06-08 | 2009-03-15 | Sod Conseils Rech Applic | Chimere somatostatin-dopamin-analoga |
| ATE346084T1 (de) * | 2002-02-27 | 2006-12-15 | Ferring Bv | Zwischenprodukte und verfahren zur herstellung von heptapeptid-oxytocinanaloga |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US20070093420A1 (en) | 2005-08-26 | 2007-04-26 | Yeomans David C | Therapy procedure for drug delivery for trigeminal pain |
| DK1787658T3 (da) | 2005-11-10 | 2012-06-25 | Chemi Spa | Formuleringer med forsinket frigørelse og indeholdende somatostatin-analoge væksthormoninhibitorer |
| WO2008011168A2 (en) * | 2006-07-21 | 2008-01-24 | Amgen Inc. | Glycosylated peptide antagonists of the bradykinin b1 receptor |
| WO2008095063A1 (en) | 2007-01-31 | 2008-08-07 | Dana-Farber Cancer Institute, Inc. | Stabilized p53 peptides and uses thereof |
| ES2430067T3 (es) | 2007-03-28 | 2013-11-18 | President And Fellows Of Harvard College | Polipéptidos cosidos |
| CN101821281A (zh) | 2007-09-25 | 2010-09-01 | 格礼卡姆股份公司 | 糖蛋白和糖基化的细胞以及其制备方法 |
| AU2008323683B2 (en) * | 2007-11-09 | 2014-10-02 | University Of Tennessee Research Foundation | Anti-inflammatory quinic acid derivatives for oral administration |
| ES2750651T3 (es) | 2008-06-12 | 2020-03-26 | Ipsen Bioinnovation Ltd | Proteínas de fusión para uso en el tratamiento de acromegalia |
| US10240138B2 (en) | 2008-06-12 | 2019-03-26 | Ipsen Bioinnovation Limited | Polypeptides that bind to and inhibit secretion from growth hormone secreting cells |
| US8377891B2 (en) | 2008-11-07 | 2013-02-19 | Usv, Ltd. | Process for synthesis of cyclic octapeptide |
| GB0820970D0 (en) | 2008-11-17 | 2008-12-24 | Syntaxin Ltd | Suppression of cancer |
| DK2603600T3 (da) | 2010-08-13 | 2019-03-04 | Aileron Therapeutics Inc | Peptidomimetiske makrocyklusser |
| SG10201601327RA (en) | 2011-09-04 | 2016-03-30 | Glytech Inc | Glycosylated polypeptide and drug composition containing said polypeptide |
| CN103930441B (zh) | 2011-09-04 | 2017-11-17 | 株式会社糖锁工学研究所 | 附加糖链的多肽和含有该多肽的医药组合物 |
| CA2852468A1 (en) | 2011-10-18 | 2013-04-25 | Aileron Therapeutics, Inc. | Peptidomimetic macrocyles |
| HK1205454A1 (en) | 2012-02-15 | 2015-12-18 | Aileron Therapeutics, Inc. | Triazole-crosslinked and thioether-crosslinked peptidomimetic macrocycles |
| SG10201606775YA (en) | 2012-02-15 | 2016-10-28 | Aileron Therapeutics Inc | Peptidomimetic macrocycles |
| CA2887285A1 (en) | 2012-11-01 | 2014-05-08 | Aileron Therapeutics, Inc. | Disubstituted amino acids and methods of preparation and use thereof |
| DK3007704T3 (da) | 2013-06-13 | 2021-03-29 | Antisense Therapeutics Ltd | Kombinationsterapi til akromegali |
| JP2017533889A (ja) | 2014-09-24 | 2017-11-16 | エルロン・セラピューティクス・インコーポレイテッドＡｉｌｅｒｏｎ Ｔｈｅｒａｐｅｕｔｉｃｓ，Ｉｎｃ． | ペプチド模倣大環状分子およびその使用 |
| HRP20231438T1 (hr) | 2015-01-07 | 2024-06-07 | Tonix Pharma Limited | Formulacije oksitocina koje sadrže magnezij i načini uporabe |
| JP2018516844A (ja) | 2015-03-20 | 2018-06-28 | エルロン・セラピューティクス・インコーポレイテッドＡｉｌｅｒｏｎ Ｔｈｅｒａｐｅｕｔｉｃｓ，Ｉｎｃ． | ペプチド模倣大環状分子およびその使用 |
| JP7093559B2 (ja) | 2016-04-12 | 2022-06-30 | トライジェミナ， インコーポレイテッド | マグネシウム含有オキシトシン製剤および使用の方法 |
| WO2019104214A1 (en) | 2017-11-22 | 2019-05-31 | Dauntless 2, Inc. | Membrane emulsification device for microsphere creation |
| WO2019104225A1 (en) | 2017-11-22 | 2019-05-31 | Dauntless 2, Inc. | Therapeutic compound formulations |
| WO2020005842A1 (en) | 2018-06-25 | 2020-01-02 | Dauntless 2, Inc. | Membrane emulsification device with impeller for microsphere creation |
| CN114026107A (zh) | 2019-04-16 | 2022-02-08 | 巴克姆股份公司 | 二硫键肽的生产 |
| EP4135698A4 (en) | 2020-04-17 | 2024-08-14 | The Trustees of Indiana University | SMALL MOLECULE ANTIVIRAL DRUG TREATMENT FOR HUMAN PAPILLOMAVIRUS INFECTIONS |
| WO2022087385A1 (en) * | 2020-10-22 | 2022-04-28 | The Trustees Of Indiana University | Molecular designs of glucose-responsive and glucose-cleavable insulin analogues |
| WO2025229200A1 (en) | 2024-05-03 | 2025-11-06 | Bachem Holding Ag | Manufacture of disulfide bonded peptides |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4254023A (en) * | 1979-10-16 | 1981-03-03 | Pennwalt Corporation | Synthesis of peptide alcohols by the solid phase method |
| US4280953A (en) * | 1979-11-08 | 1981-07-28 | The Salk Institute For Biological Studies | Glycosylated analogs of somatostatin |
| DE19375086I2 (de) * | 1979-11-27 | 2003-01-09 | Novartis Ag | Polypeptide Verfahren zu ihrer Herstellung pharmazeutische Zusammensetzungen die diese Polypeptide enthalten und ihre Verwendung |
| FR2522967B1 (fr) * | 1982-03-15 | 1986-03-07 | Anvar | Conjugues d'haptenes et de muramyl-peptides, doues d'activite immunogene et compositions les contenant |
| US4483792A (en) * | 1982-11-17 | 1984-11-20 | Kim Wan S | Glycosylated insulin derivatives |
| US4444683A (en) * | 1982-11-17 | 1984-04-24 | University Of Utah | Glycosylated insulin derivatives |
| FR2546163B1 (fr) * | 1983-05-16 | 1987-10-09 | Centre Nat Rech Scient | Nouveaux derives acyles hydrosolubles de peptides ou d'amino-acides, leur preparation et leur application |
| FR2548673B1 (fr) * | 1983-07-05 | 1985-10-04 | Essilor Int | Polymeres supports de produits actifs relargables et leur procede de preparation |
| LU85269A1 (fr) * | 1984-03-26 | 1985-10-14 | Techland S A | Composes nouveaux de somatostatine,procede pour leur synthese,preparation a usage veterinaire contenant lesdits composes et procede pour le traitement d'animaux |
| US4564998A (en) * | 1984-10-19 | 1986-01-21 | Westinghouse Electric Corp. | Coil winding methods and apparatus |
| DE3439610A1 (de) * | 1984-10-30 | 1986-04-30 | Boehringer Mannheim Gmbh, 6800 Mannheim | Immunogene, verfahren zu deren herstellung sowie damit gewonnene antikoerper gegen glykosiliertes haemoglobin |
| FI860708A7 (fi) * | 1985-02-20 | 1986-08-21 | Ciba Geigy Ag | Acylerade hexosderivat och foerfarande foer deras framstaellning. |
| JPS61264260A (ja) * | 1985-05-17 | 1986-11-22 | Rikagaku Kenkyusho | アルデヒド化多孔性高分子材料によるタンパク質の除去方法 |
| AU597909B2 (en) * | 1985-10-09 | 1990-06-14 | Procter & Gamble Company, The | Granular detergent compositions having improved solubility |
| SE8506094D0 (sv) * | 1985-12-20 | 1985-12-20 | Astra Laekemedel Ab | New antibacterial agents and intermediates therefor |
| JPS63165410A (ja) * | 1986-09-11 | 1988-07-08 | Tokyo Organ Chem Ind Ltd | アルデヒド基を有する架橋共重合体の製造方法 |
| JPS63165411A (ja) * | 1986-09-11 | 1988-07-08 | Tokyo Organ Chem Ind Ltd | アルデヒド基を有する架橋共重合体の製法 |
| HU906340D0 (en) * | 1986-10-13 | 1991-04-29 | Sandoz Ag | Synthesis in solid phase for producing peptonic alcohols |
| US4859736A (en) * | 1987-03-30 | 1989-08-22 | Ciba-Geigy Corporation | Synthetic polystyrene resin and its use in solid phase peptide synthesis |
| CH679045A5 (OSRAM) * | 1987-06-29 | 1991-12-13 | Sandoz Ag |
-
1987
- 1987-10-01 HU HU906340A patent/HU906340D0/hu unknown
- 1987-10-01 HU HU874432A patent/HU206890B/hu not_active IP Right Cessation
- 1987-10-01 HU HU906341A patent/HU906341D0/hu unknown
- 1987-10-01 NL NL8702345A patent/NL194729C/nl not_active IP Right Cessation
- 1987-10-07 LU LU87014A patent/LU87014A1/fr unknown
- 1987-10-07 FR FR8713949A patent/FR2609991A1/fr active Granted
- 1987-10-09 BE BE8701187A patent/BE1003752A4/fr not_active IP Right Cessation
- 1987-10-09 GB GB8723737A patent/GB2199829B/en not_active Expired - Lifetime
- 1987-10-12 CH CH1353/89A patent/CH682632A5/de not_active IP Right Cessation
- 1987-10-12 NZ NZ222133A patent/NZ222133A/xx unknown
- 1987-10-12 PT PT85904A patent/PT85904B/pt unknown
- 1987-10-12 DK DK198705327A patent/DK174337B1/da not_active IP Right Cessation
- 1987-10-12 CH CH3804/90A patent/CH680512A5/de not_active IP Right Cessation
- 1987-10-12 AU AU79564/87A patent/AU617986B2/en not_active Ceased
- 1987-10-12 WO PCT/EP1987/000593 patent/WO1988002756A2/en not_active Ceased
- 1987-10-12 JP JP62257047A patent/JPH0645639B2/ja not_active Expired - Lifetime
- 1987-10-12 SE SE8703938A patent/SE8703938L/ not_active Application Discontinuation
- 1987-10-12 GR GR871567A patent/GR871567B/el unknown
- 1987-10-12 PL PL1987268173A patent/PL157156B1/pl unknown
- 1987-10-12 KR KR1019870011265A patent/KR960016861B1/ko not_active Expired - Lifetime
- 1987-10-12 FI FI874495A patent/FI874495A7/fi not_active Application Discontinuation
- 1987-10-12 DE DE19873790635 patent/DE3790635T1/de active Pending
- 1987-10-13 ES ES8702913A patent/ES2007418A6/es not_active Expired
- 1987-10-13 CA CA000549140A patent/CA1340985C/en not_active Expired - Lifetime
-
1988
- 1988-01-12 GB GB8800537A patent/GB2199831B/en not_active Expired - Lifetime
-
1990
- 1990-06-04 JP JP2147161A patent/JP2744910B2/ja not_active Expired - Lifetime
-
1991
- 1991-07-03 AU AU80150/91A patent/AU634664B2/en not_active Expired
- 1991-07-12 IE IE244291A patent/IE912442A1/en unknown
-
1993
- 1993-04-07 SE SE9301172A patent/SE518630C2/sv unknown
-
1994
- 1994-07-07 US US08/272,704 patent/US5656721A/en not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NL194729C (nl) | Werkwijze voor de bereiding van peptidealcoholen via vaste fase. | |
| RU2318004C2 (ru) | Добавки в виде полиалкиленгликолевой кислоты | |
| Ede et al. | A simple linker for the attachment of aldehydes to the solid phase. Application to solid phase synthesis by the multipin™ method | |
| JP4607017B2 (ja) | アミノ化複合型糖鎖誘導体及びその製造方法 | |
| JPH04501121A (ja) | 生物学的に活性な新規薬剤・ポリマー誘導体およびその製造方法 | |
| US3814732A (en) | Modified solid supports for solid phase synthesis | |
| Kim et al. | Polymer attached cyclic dipeptides as catalysts for enantioselective cyanohydrin formation | |
| US4831084A (en) | Resin-linker combination for the solid-phase synthesis of peptides and intermediates | |
| US4315074A (en) | Molecular transformation procedure | |
| NL8104079A (nl) | Werkwijze voor het veresteren van alfa-l-asparty-l-fenylalanine. | |
| US4254023A (en) | Synthesis of peptide alcohols by the solid phase method | |
| JPH0632790A (ja) | ビオチン導入試薬およびそれを用いる合成ペプチド精製法 | |
| Johnson et al. | JANTHINOCINS A, B AND C, NOVEL PEPTIDE LACTONE ANTIBIOTICS PRODUCED BY JANTHINOBACTERIUM LIVIDUM II. STRUCTURE ELUCIDATION | |
| WO1991019984A1 (en) | Carboxyl-terminal protein sequencing method and apparatus | |
| CN114315957B (zh) | 一种多肽的制备方法 | |
| US7420035B2 (en) | Purification of polypeptides | |
| JPH03503958A (ja) | カルシトニン遺伝子関連ペプチドの製造方法 | |
| CN110498835B (zh) | 一种合成etelcalcetide的方法 | |
| CN111378009A (zh) | 一种奥曲肽的制备方法 | |
| EP0001174B1 (en) | A peptide and the salts thereof, processes for their preparation and compositions containing them | |
| CA1315470C (en) | Allylic side chain-containing solid phase systems, processes for the preparation thereof and the use thereof in solid phase reactions | |
| CN117024476A (zh) | 一种二苯基膦酰氧基-x-苯酚类化合物、制备方法及制备阿斯巴甜中的应用 | |
| FI99113B (fi) | Peptidialkoholien kiinteän faasin synteesi | |
| KR101171095B1 (ko) | 루프로라이드의 제조방법 | |
| Tjoeng et al. | 4-(2-Chloropropionyl) phenylacetoxy-polyethylene glycol: a new photolabile support for liquid phase peptide synthesis |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| CNR | Transfer of rights (patent application after its laying open for public inspection) |
Free format text: NOVARTIS AG |
|
| V4 | Discontinued because of reaching the maximum lifetime of a patent |
Effective date: 20071001 |