PL81109B1 - Partially protected basic amino acids and peptides[ca928315a] - Google Patents

Partially protected basic amino acids and peptides[ca928315a] Download PDF

Info

Publication number: PL81109B1
Authority: PL; Poland
Prior art keywords: group; general formula; compound; acylated; complex
Prior art date: 1969-07-03

Application number

PL14171970A

Other languages

English (en)

Polish (pl)

Original Assignee

Richter Gedeon Vegyeszeti Gyar Rt

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1969-07-03

Filing date

1970-07-01

Publication date

1975-08-30

1970-07-01 Application filed by Richter Gedeon Vegyeszeti Gyar Rt filed Critical Richter Gedeon Vegyeszeti Gyar Rt

1975-08-30 Publication of PL81109B1 publication Critical patent/PL81109B1/pl

Links

150000001413 amino acids Chemical class 0.000 title claims abstract description 7
108090000765 processed proteins & peptides Proteins 0.000 title abstract description 3
102000004196 processed proteins & peptides Human genes 0.000 title abstract description 3
150000003839 salts Chemical class 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 17
238000000034 method Methods 0.000 claims description 10
-1 metal complex compound Chemical class 0.000 claims description 8
239000004472 Lysine Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
235000001014 amino acid Nutrition 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
125000000962 organic group Chemical group 0.000 claims description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
125000000524 functional group Chemical group 0.000 claims description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
239000003795 chemical substances by application Substances 0.000 claims 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 1
125000005907 alkyl ester group Chemical group 0.000 claims 1
150000001371 alpha-amino acids Chemical class 0.000 claims 1
235000008206 alpha-amino acids Nutrition 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 abstract description 4
239000001257 hydrogen Substances 0.000 abstract description 3
208000025865 Ulcer Diseases 0.000 abstract 1
150000002829 nitrogen Chemical class 0.000 abstract 1
231100000397 ulcer Toxicity 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000203 mixture Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
125000004433 nitrogen atom Chemical group N* 0.000 description 6
238000001816 cooling Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229940024606 amino acid Drugs 0.000 description 4
238000010348 incorporation Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
210000000845 cartilage Anatomy 0.000 description 3
150000004699 copper complex Chemical class 0.000 description 3
229940088598 enzyme Drugs 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
229920002683 Glycosaminoglycan Polymers 0.000 description 2
BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
235000011148 calcium chloride Nutrition 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229940116318 copper carbonate Drugs 0.000 description 2
BWFPGXWASODCHM-UHFFFAOYSA-N copper monosulfide Chemical compound [Cu]=S BWFPGXWASODCHM-UHFFFAOYSA-N 0.000 description 2
229910000009 copper(II) carbonate Inorganic materials 0.000 description 2
GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 2
239000011646 cupric carbonate Substances 0.000 description 2
235000019854 cupric carbonate Nutrition 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000004922 lacquer Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
IJWMYYIUFNJDKN-UHFFFAOYSA-N (4-chlorophenyl)methyl carbonochloridate Chemical compound ClC(=O)OCC1=CC=C(Cl)C=C1 IJWMYYIUFNJDKN-UHFFFAOYSA-N 0.000 description 1
102000029816 Collagenase Human genes 0.000 description 1
108060005980 Collagenase Proteins 0.000 description 1
108010016626 Dipeptides Proteins 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
108060005987 Kallikrein Proteins 0.000 description 1
102000001399 Kallikrein Human genes 0.000 description 1
229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
108010067372 Pancreatic elastase Proteins 0.000 description 1
102000016387 Pancreatic elastase Human genes 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
102000035195 Peptidases Human genes 0.000 description 1
108010059712 Pronase Proteins 0.000 description 1
241000700159 Rattus Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000000767 anti-ulcer Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229960002424 collagenase Drugs 0.000 description 1
210000002808 connective tissue Anatomy 0.000 description 1
210000001608 connective tissue cell Anatomy 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
239000011874 heated mixture Substances 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
235000018977 lysine Nutrition 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
208000011906 peptic ulcer disease Diseases 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000002753 trypsin inhibitor Substances 0.000 description 1
229960004441 tyrosine Drugs 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
- C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain 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
- 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
- C07K1/064—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 for omega-amino or -guanidino functions

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Analytical Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Peptides Or Proteins (AREA)

PL14171970A 1969-07-03 1970-07-01 Partially protected basic amino acids and peptides[ca928315a] PL81109B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HURI000374		1969-07-03

Publications (1)

Publication Number	Publication Date
PL81109B1 true PL81109B1 (en)	1975-08-30

Family

ID=11000829

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL14171970A PL81109B1 (en)	1969-07-03	1970-07-01	Partially protected basic amino acids and peptides[ca928315a]

Country Status (8)

Country	Link
AT (1)	AT302351B (de)
BE (1)	BE752845A (de)
CA (1)	CA928315A (de)
DE (1)	DE2032329A1 (de)
ES (1)	ES381363A1 (de)
FR (1)	FR2059474A1 (de)
NL (1)	NL7009736A (de)
PL (1)	PL81109B1 (de)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL6717029A (de) *	1968-01-29	1969-06-17

1970
- 1970-06-19 AT AT551870A patent/AT302351B/de not_active IP Right Cessation
- 1970-06-30 DE DE19702032329 patent/DE2032329A1/de active Pending
- 1970-07-01 PL PL14171970A patent/PL81109B1/pl unknown
- 1970-07-01 NL NL7009736A patent/NL7009736A/xx unknown
- 1970-07-02 BE BE752845A patent/BE752845A/xx unknown
- 1970-07-02 ES ES381363A patent/ES381363A1/es not_active Expired
- 1970-07-03 CA CA087182A patent/CA928315A/en not_active Expired
- 1970-07-03 FR FR7024830A patent/FR2059474A1/fr active Granted

Also Published As

Publication number	Publication date
ES381363A1 (es)	1972-11-01
CA928315A (en)	1973-06-12
AT302351B (de)	1972-10-10
FR2059474A1 (en)	1971-06-04
DE2032329A1 (de)	1971-01-28
FR2059474B1 (de)	1974-07-12
BE752845A (fr)	1970-12-16
NL7009736A (de)	1971-01-05

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CA1051802A (en)	1979-04-03	Amino acid derivatives and a process for the preparation thereof
PL81109B1 (en)	1975-08-30	Partially protected basic amino acids and peptides[ca928315a]
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