NO311892B1 - Syklopeptider, fremgangsmåte for fremstilling derav, farmasöytiske preparater, fremgangsmåte for fremstilling derav,samt anvendelse av forbindelsene - Google Patents

Syklopeptider, fremgangsmåte for fremstilling derav, farmasöytiske preparater, fremgangsmåte for fremstilling derav,samt anvendelse av forbindelsene Download PDF

Info

Publication number: NO311892B1
Authority: NO; Norway
Prior art keywords: asp; gly; arg; cyclo; formula
Prior art date: 1994-04-30

Application number

NO19951645A

Other languages

English (en)

Norwegian (no)

Other versions

NO951645D0 (no

NO951645L (no

Inventor

Alfred Jonczyk

Guenter Hoelzemann

Simon Goodmann

Horst Kessler

Roland Haubner

Jochen Wermuth

Original Assignee

Merck Patent Gmbh

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.)

1994-04-30

Filing date

1995-04-28

Publication date

2002-02-11

1995-04-28 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1995-04-28 Publication of NO951645D0 publication Critical patent/NO951645D0/no

1995-10-31 Publication of NO951645L publication Critical patent/NO951645L/no

2002-02-11 Publication of NO311892B1 publication Critical patent/NO311892B1/no

Links

102000001189 Cyclic Peptides Human genes 0.000 title claims abstract description 8
108010069514 Cyclic Peptides Proteins 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 title claims description 50
238000000034 method Methods 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 15
239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
150000003839 salts Chemical class 0.000 claims abstract description 18
108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 15
108010044426 integrins Proteins 0.000 claims abstract description 8
102000006495 integrins Human genes 0.000 claims abstract description 8
238000011282 treatment Methods 0.000 claims abstract description 8
239000003814 drug Substances 0.000 claims abstract description 6
239000003446 ligand Substances 0.000 claims abstract description 6
238000001042 affinity chromatography Methods 0.000 claims abstract description 5
201000010099 disease Diseases 0.000 claims abstract description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 5
SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims abstract description 4
AHYSOLBMJMYWIH-UHFFFAOYSA-N 2-(3-amino-2-oxo-1,3-dihydropyrrol-4-yl)-4-methylpentanoic acid Chemical compound CC(C)CC(C1=CNC(=O)C1N)C(=O)O AHYSOLBMJMYWIH-UHFFFAOYSA-N 0.000 claims abstract description 3
239000002253 acid Substances 0.000 claims description 15
150000007513 acids Chemical class 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 5
238000000746 purification Methods 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 4
150000007514 bases Chemical class 0.000 claims description 2
239000002552 dosage form Substances 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
239000007788 liquid Substances 0.000 claims 2
238000002347 injection Methods 0.000 abstract description 5
239000007924 injection Substances 0.000 abstract description 5
208000006011 Stroke Diseases 0.000 abstract description 3
230000000845 anti-microbial effect Effects 0.000 abstract description 3
239000007943 implant Substances 0.000 abstract description 3
WUUZOAUUYYEMOV-UHFFFAOYSA-N 2-[5-(aminomethyl)thiophen-2-yl]acetic acid Chemical compound NCC1=CC=C(CC(O)=O)S1 WUUZOAUUYYEMOV-UHFFFAOYSA-N 0.000 abstract description 2
206010002383 Angina Pectoris Diseases 0.000 abstract description 2
206010003210 Arteriosclerosis Diseases 0.000 abstract description 2
206010008190 Cerebrovascular accident Diseases 0.000 abstract description 2
206010061218 Inflammation Diseases 0.000 abstract description 2
206010028980 Neoplasm Diseases 0.000 abstract description 2
208000001132 Osteoporosis Diseases 0.000 abstract description 2
208000007536 Thrombosis Diseases 0.000 abstract description 2
229960002684 aminocaproic acid Drugs 0.000 abstract description 2
230000000840 anti-viral effect Effects 0.000 abstract description 2
208000011775 arteriosclerosis disease Diseases 0.000 abstract description 2
230000000747 cardiac effect Effects 0.000 abstract description 2
230000004054 inflammatory process Effects 0.000 abstract description 2
239000003112 inhibitor Substances 0.000 abstract description 2
230000003993 interaction Effects 0.000 abstract description 2
LCSRWEJPYNVBGR-UHFFFAOYSA-N 2-(1,7-diazaspiro[4.4]nonan-7-yl)-4-methylpentanoic acid Chemical compound C1N(C(CC(C)C)C(O)=O)CCC11NCCC1 LCSRWEJPYNVBGR-UHFFFAOYSA-N 0.000 abstract 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
206010061216 Infarction Diseases 0.000 abstract 1
108010020950 Integrin beta3 Proteins 0.000 abstract 1
210000000988 bone and bone Anatomy 0.000 abstract 1
239000000645 desinfectant Substances 0.000 abstract 1
230000007574 infarction Effects 0.000 abstract 1
108010021518 integrin beta5 Proteins 0.000 abstract 1
230000002265 prevention Effects 0.000 abstract 1
-1 4-methoxy-2,3,6-trimethylphenylsulfonyl Chemical group 0.000 description 19
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
125000006239 protecting group Chemical group 0.000 description 17
239000000243 solution Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
229920000642 polymer Polymers 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
239000007858 starting material Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
235000011054 acetic acid Nutrition 0.000 description 5
125000002252 acyl group Chemical group 0.000 description 5
235000001014 amino acid Nutrition 0.000 description 5
229940024606 amino acid Drugs 0.000 description 5
150000001413 amino acids Chemical class 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000003480 eluent Substances 0.000 description 4
238000007327 hydrogenolysis reaction Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
238000010647 peptide synthesis reaction Methods 0.000 description 4
230000007017 scission Effects 0.000 description 4
239000007921 spray Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 3
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
125000000539 amino acid group Chemical group 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
235000003704 aspartic acid Nutrition 0.000 description 3
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
102000004196 processed proteins & peptides Human genes 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 2
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 2
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
239000004472 Lysine Substances 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
229920005654 Sephadex Polymers 0.000 description 2
239000012507 Sephadex™ Substances 0.000 description 2
KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical compound CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
238000000576 coating method Methods 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 2
239000012154 double-distilled water Substances 0.000 description 2
239000008298 dragée Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000003889 eye drop Substances 0.000 description 2
229940012356 eye drops Drugs 0.000 description 2
238000010265 fast atom bombardment Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
235000013922 glutamic acid Nutrition 0.000 description 2
239000004220 glutamic acid Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
239000002674 ointment Substances 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
239000012071 phase Substances 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000003380 propellant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000003797 solvolysis reaction Methods 0.000 description 2
239000008347 soybean phospholipid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
OIXLLKLZKCBCPS-RZVRUWJTSA-N (2s)-2-azanyl-5-[bis(azanyl)methylideneamino]pentanoic acid Chemical compound OC(=O)[C@@H](N)CCCNC(N)=N.OC(=O)[C@@H](N)CCCNC(N)=N OIXLLKLZKCBCPS-RZVRUWJTSA-N 0.000 description 1
DVBUCBXGDWWXNY-SFHVURJKSA-N (2s)-5-(diaminomethylideneamino)-2-(9h-fluoren-9-ylmethoxycarbonylamino)pentanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CCCN=C(N)N)C(O)=O)C3=CC=CC=C3C2=C1 DVBUCBXGDWWXNY-SFHVURJKSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
DFPYXQYWILNVAU-UHFFFAOYSA-N 1-hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1.C1=CC=C2N(O)N=NC2=C1 DFPYXQYWILNVAU-UHFFFAOYSA-N 0.000 description 1
OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 1
YVOOPGWEIRIUOX-UHFFFAOYSA-N 2-azanyl-3-sulfanyl-propanoic acid Chemical compound SCC(N)C(O)=O.SCC(N)C(O)=O YVOOPGWEIRIUOX-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
125000000030 D-alanine group Chemical group [H]N([H])[C@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 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 description 1
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 description 1
QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
238000006845 Michael addition reaction Methods 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
229920002684 Sepharose Polymers 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
239000012317 TBTU Substances 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
239000004473 Threonine Substances 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
241000700605 Viruses Species 0.000 description 1
CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
150000003926 acrylamides Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
150000003862 amino acid derivatives Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
238000004873 anchoring Methods 0.000 description 1
230000033115 angiogenesis Effects 0.000 description 1
238000002399 angioplasty Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
229940064004 antiseptic throat preparations Drugs 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
108010072041 arginyl-glycyl-aspartic acid Proteins 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 1
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000009582 asparagine Nutrition 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
239000012620 biological material Substances 0.000 description 1
LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical compound O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000004899 c-terminal region Anatomy 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
150000005827 chlorofluoro hydrocarbons Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229960004106 citric acid Drugs 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000006196 drop Substances 0.000 description 1
239000000890 drug combination Substances 0.000 description 1
230000002500 effect on skin Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000029142 excretion Effects 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000002523 gelfiltration Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
229950006191 gluconic acid Drugs 0.000 description 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
235000013773 glyceryl triacetate Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000001802 infusion Methods 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
230000014759 maintenance of location Effects 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
125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical class C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 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
239000011664 nicotinic acid Substances 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000000010 osteolytic effect Effects 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-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
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000011321 prophylaxis Methods 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
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
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012064 sodium phosphate buffer Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000010532 solid phase synthesis reaction Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
238000002560 therapeutic procedure Methods 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
230000007306 turnover Effects 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
230000029663 wound healing Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/745—Blood coagulation or fibrinolysis factors
- C07K14/75—Fibrinogen
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- C07K5/10—Tetrapeptides
- C07K5/1019—Tetrapeptides 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
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/52—Cyclic peptides containing at least one abnormal peptide link with only normal peptide links in the ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/27—Cyclic peptide or cyclic protein

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Molecular Biology (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Hematology (AREA)
Gastroenterology & Hepatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Zoology (AREA)
Toxicology (AREA)
Communicable Diseases (AREA)
Vascular Medicine (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Oncology (AREA)
Immunology (AREA)
Epidemiology (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)

NO19951645A 1994-04-30 1995-04-28 Syklopeptider, fremgangsmåte for fremstilling derav, farmasöytiske preparater, fremgangsmåte for fremstilling derav,samt anvendelse av forbindelsene NO311892B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4415310A DE4415310A1 (de)	1994-04-30	1994-04-30	Cyclopeptide

Publications (3)

Publication Number	Publication Date
NO951645D0 NO951645D0 (no)	1995-04-28
NO951645L NO951645L (no)	1995-10-31
NO311892B1 true NO311892B1 (no)	2002-02-11

Family

ID=6516993

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19951645A NO311892B1 (no)	1994-04-30	1995-04-28	Syklopeptider, fremgangsmåte for fremstilling derav, farmasöytiske preparater, fremgangsmåte for fremstilling derav,samt anvendelse av forbindelsene

Country Status (21)

Country	Link
US (1)	US5693612A (cs)
EP (1)	EP0683173B1 (cs)
JP (1)	JP3711154B2 (cs)
KR (1)	KR100360831B1 (cs)
CN (1)	CN1161374C (cs)
AT (1)	ATE183199T1 (cs)
AU (1)	AU697614B2 (cs)
CA (1)	CA2148194C (cs)
CZ (1)	CZ286705B6 (cs)
DE (2)	DE4415310A1 (cs)
DK (1)	DK0683173T3 (cs)
ES (1)	ES2137394T3 (cs)
GR (1)	GR3031696T3 (cs)
HU (1)	HU216795B (cs)
NO (1)	NO311892B1 (cs)
PL (1)	PL181272B1 (cs)
RU (1)	RU2151776C1 (cs)
SK (1)	SK281843B6 (cs)
TW (1)	TW354790B (cs)
UA (1)	UA46699C2 (cs)
ZA (1)	ZA953467B (cs)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7244622B2 (en) *	1996-04-03	2007-07-17	Applera Corporation	Device and method for multiple analyte detection
DE19736772A1 (de) *	1997-08-23	1999-02-25	Merck Patent Gmbh	Cyclopeptidderivate
AU2592600A (en)	1998-12-23	2000-07-31	G.D. Searle & Co.	Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
CA2439852A1 (en) *	2001-03-02	2002-09-12	Christine Dingivan	Methods of preventing or treating inflammatory or autoimmune disorders by administering integrin alphav beta3 antagonists
CA2478317A1 (en) *	2002-03-04	2003-09-18	Medimmune, Inc.	Methods of preventing or treating disorders by administering an integrin .alpha.v.beta.3 antagonist in combination with an hmg-coa reductase inhibitor or a bisphosphonate
WO2003075957A1 (en) *	2002-03-04	2003-09-18	Medimmune, Inc.	The prevention or treatment of cancer using integrin alphavbeta3 antagonists in combination with other agents
WO2003086458A1 (en)	2002-04-12	2003-10-23	Medimmune, Inc.	Recombinant anti-interleukin-9 antibodies
WO2004066956A2 (en) *	2003-01-30	2004-08-12	Medimmune, Inc.	Uses of integrin alphavbeta3 antagonists
AU2004229501B2 (en)	2003-04-11	2011-08-18	Medimmune, Llc	Recombinant IL-9 antibodies and uses thereof
CN100429223C (zh) *	2004-02-06	2008-10-29	南京工业大学	环(d-苯丙-d-组)二肽的制备方法
US7351739B2 (en) *	2004-04-30	2008-04-01	Wellgen, Inc.	Bioactive compounds and methods of uses thereof
PT2484365E (pt)	2004-06-04	2013-12-12	Scripps Research Inst	Composições e métodos para o tratamento de doenças neovasculares
US20060116316A1 (en) *	2004-10-14	2006-06-01	Kinsella Todd M	Heterocyclic inhibitors of IRES-mediated translation and methods of use thereof
CA2585717A1 (en)	2004-10-27	2006-05-04	Medimmune Inc.	Modulation of antibody specificity by tailoring the affinity to cognate antigens
WO2006048473A1 (es) *	2004-10-30	2006-05-11	Universidad Del Pais Vasco/Euskal Herriko Unibertsitatea	CICLOPÉPTIDOS RGD β-LACTÁMINOS GIROS GAMMA (Ϝ)
EP2043603A4 (en)	2006-07-11	2010-10-27	Arubor Corp	PREVENTION AND THERAPY OF RHINOSINUSITIS WITH PROINFLAMMATORY CYTOKINHERMERS
HUE048024T2 (hu)	2006-08-10	2020-05-28	Roy C Levitt	Anakinra bronchiolitis obliterans szindróma kezelésében való alkalmazásra
PT2408802T (pt) *	2009-03-16	2017-08-03	Governing Council Univ Toronto	Moléculas de aminoácido ciclicas e métodos para as preparar
SI3350222T1 (sl) *	2015-09-18	2022-01-31	Technische Universitaet Muenchen	Ligandi za integrin avbeta6, sinteza in uporaba le-teh
US11072616B2 (en)	2015-11-11	2021-07-27	Universite De Montreal	Cyclic peptides targeting alpha-4-beta-7 integrin
ES2884107T3 (es)	2016-11-11	2021-12-10	Zealand Pharma As	Multímeros de péptidos cíclicos con diana en la integrina alfa-4 beta-7
EP3388445A1 (en) *	2017-04-10	2018-10-17	F. Hoffmann-La Roche AG	Peptide macrocycles and use thereof in the treatment of bacterial infections
US11286281B2 (en)	2017-05-10	2022-03-29	Zealand Pharma A/S	Homodetic cyclic peptides targeting alpha-4-beta-7 integrin

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4472305A (en) *	1983-05-17	1984-09-18	Sterling Drug Inc.	Hexapeptide amides
DE3703159A1 (de) *	1987-02-03	1988-08-11	Hoechst Ag	Cyclische peptide mit cytoprotektiver wirkung
JP2945680B2 (ja) *	1988-09-09	1999-09-06	旭硝子株式会社	ペプチド誘導体およびその用途
DE3915361A1 (de) *	1989-05-11	1990-11-15	Merck Patent Gmbh	Cyclopeptide
US5192746A (en) *	1990-07-09	1993-03-09	Tanabe Seiyaku Co., Ltd.	Cyclic cell adhesion modulation compounds
AU666853B2 (en) *	1991-04-05	1996-02-29	Genentech Inc.	Platelet aggregation inhibitors having high specificity for GP IIbIIIa
ATE155486T1 (de) *	1991-08-13	1997-08-15	Takeda Chemical Industries Ltd	Zyklische peptide und ihre verwendung
IL103252A (en) *	1991-09-30	1997-03-18	Du Pont Merck Pharma	CYCLIC COMPOUNDS USEFUL AS INHIBITORS OF PLATELET GLYCOPROTEIN IIb/IIIa AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
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
DE4310643A1 (de) *	1993-04-01	1994-10-06	Merck Patent Gmbh	Cyclische Adhäsionsinhibitoren

1994
- 1994-04-30 DE DE4415310A patent/DE4415310A1/de not_active Withdrawn
1995
- 1995-04-21 UA UA95048361A patent/UA46699C2/uk unknown
- 1995-04-26 CZ CZ19951073A patent/CZ286705B6/cs not_active IP Right Cessation
- 1995-04-26 EP EP95106259A patent/EP0683173B1/de not_active Expired - Lifetime
- 1995-04-26 DK DK95106259T patent/DK0683173T3/da active
- 1995-04-26 DE DE59506568T patent/DE59506568D1/de not_active Expired - Lifetime
- 1995-04-26 ES ES95106259T patent/ES2137394T3/es not_active Expired - Lifetime
- 1995-04-26 AT AT95106259T patent/ATE183199T1/de active
- 1995-04-27 RU RU95106821/04A patent/RU2151776C1/ru active
- 1995-04-27 TW TW084104188A patent/TW354790B/zh active
- 1995-04-27 AU AU17724/95A patent/AU697614B2/en not_active Expired
- 1995-04-28 CA CA002148194A patent/CA2148194C/en not_active Expired - Lifetime
- 1995-04-28 US US08/430,238 patent/US5693612A/en not_active Expired - Lifetime
- 1995-04-28 ZA ZA953467A patent/ZA953467B/xx unknown
- 1995-04-28 NO NO19951645A patent/NO311892B1/no not_active IP Right Cessation
- 1995-04-28 HU HU9501253A patent/HU216795B/hu not_active IP Right Cessation
- 1995-04-28 CN CNB951052004A patent/CN1161374C/zh not_active Expired - Lifetime
- 1995-04-28 PL PL95308420A patent/PL181272B1/pl not_active IP Right Cessation
- 1995-04-28 JP JP10665595A patent/JP3711154B2/ja not_active Expired - Lifetime
- 1995-04-28 KR KR1019950010234A patent/KR100360831B1/ko not_active Expired - Fee Related
- 1995-04-28 SK SK558-95A patent/SK281843B6/sk unknown
1999
- 1999-11-03 GR GR990402787T patent/GR3031696T3/el unknown

Also Published As

Publication number	Publication date
HUT75057A (en)	1997-03-28
DK0683173T3 (da)	2000-03-13
NO951645D0 (no)	1995-04-28
CN1161374C (zh)	2004-08-11
HU216795B (hu)	1999-08-30
UA46699C2 (uk)	2002-06-17
ZA953467B (en)	1996-01-17
SK55895A3 (en)	1995-12-06
AU1772495A (en)	1995-11-09
JPH07304795A (ja)	1995-11-21
EP0683173A1 (de)	1995-11-22
DE59506568D1 (de)	1999-09-16
CZ107395A3 (en)	1995-11-15
CN1116628A (zh)	1996-02-14
NO951645L (no)	1995-10-31
KR100360831B1 (ko)	2003-01-24
US5693612A (en)	1997-12-02
ES2137394T3 (es)	1999-12-16
CA2148194A1 (en)	1995-10-31
SK281843B6 (sk)	2001-08-06
PL181272B1 (pl)	2001-07-31
RU2151776C1 (ru)	2000-06-27
GR3031696T3 (en)	2000-02-29
ATE183199T1 (de)	1999-08-15
PL308420A1 (en)	1995-11-13
HU9501253D0 (en)	1995-06-28
CZ286705B6 (en)	2000-06-14
TW354790B (en)	1999-03-21
RU95106821A (ru)	1997-01-10
KR950032275A (ko)	1995-12-20
JP3711154B2 (ja)	2005-10-26
DE4415310A1 (de)	1995-11-02
CA2148194C (en)	2007-04-10
AU697614B2 (en)	1998-10-15
EP0683173B1 (de)	1999-08-11

Legal Events

Date	Code	Title	Description
2004-12-27	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO313756B1 (no)	2002-11-25	Syklopeptidforbindelser, fremgangsmåte for fremstilling derav, farmasöytiske preparater, fremgangsmåte for fremstillingderav, samt anvdendelse av forbindelsene til fremstilling avmedikamenter og immobiliserte ligander, og til rensing av integr
RU2157379C2 (ru)	2000-10-10	Циклопептиды, способ их получения, содержащая их фармацевтическая композиция, способ ее получения
NO311892B1 (no)	2002-02-11	Syklopeptider, fremgangsmåte for fremstilling derav, farmasöytiske preparater, fremgangsmåte for fremstilling derav,samt anvendelse av forbindelsene
MXPA96004100A (en)	1997-08-01	Cyclic compounds, adhes inhibitors
CA2250861C (en)	2008-07-15	Cyclic adhesion inhibitors
US5705481A (en)	1998-01-06	Cyclopeptides
CA2102447C (en)	2007-04-10	Cyclopeptides
EP0576898A2 (en)	1994-01-05	Linear peptides