IE40930L - Decapeptides - Google Patents
DecapeptidesInfo
- Publication number
- IE40930L IE40930L IE742036A IE203674A IE40930L IE 40930 L IE40930 L IE 40930L IE 742036 A IE742036 A IE 742036A IE 203674 A IE203674 A IE 203674A IE 40930 L IE40930 L IE 40930L
- Authority
- IE
- Ireland
- Prior art keywords
- leu
- arg
- tyr
- glu
- ser
- Prior art date
Links
- 239000011347 resin Substances 0.000 abstract 6
- 229920005989 resin Polymers 0.000 abstract 6
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 4
- 125000006239 protecting group Chemical group 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 231100000252 nontoxic Toxicity 0.000 abstract 3
- 230000003000 nontoxic effect Effects 0.000 abstract 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 3
- 102000004196 processed proteins & peptides Human genes 0.000 abstract 3
- 108010029020 prolylglycine Proteins 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000005076 adamantyloxycarbonyl group Chemical group C12(CC3CC(CC(C1)C3)C2)OC(=O)* 0.000 abstract 2
- 238000003776 cleavage reaction Methods 0.000 abstract 2
- 238000010511 deprotection reaction Methods 0.000 abstract 2
- -1 nitro, tosyl Chemical group 0.000 abstract 2
- 230000007017 scission Effects 0.000 abstract 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 abstract 2
- IPVYMXZYXFFDGW-UHFFFAOYSA-N 1-methylpiperidin-4-ol;hydrochloride Chemical compound Cl.CN1CCC(O)CC1 IPVYMXZYXFFDGW-UHFFFAOYSA-N 0.000 abstract 1
- 101100188552 Arabidopsis thaliana OCT3 gene Proteins 0.000 abstract 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 abstract 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 238000005915 ammonolysis reaction Methods 0.000 abstract 1
- 229940072107 ascorbate Drugs 0.000 abstract 1
- 235000010323 ascorbic acid Nutrition 0.000 abstract 1
- 239000011668 ascorbic acid Substances 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N cinnamyl alcohol Chemical compound OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002552 dosage form Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 231100000546 inhibition of ovulation Toxicity 0.000 abstract 1
- 108010055553 leucyl-arginyl-prolyl-glycinamide Proteins 0.000 abstract 1
- 229940049920 malate Drugs 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 108010083476 phenylalanyltryptophan Proteins 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/23—Luteinising hormone-releasing hormone [LHRH]; Related peptides
-
- 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
- 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)
- Biochemistry (AREA)
- Biophysics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Endocrinology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
1458685 Decapeptides AMERICAN HOME PRODUCTS CORP 25 Sept 1974 [3 Oct 1973 21 Nov 1973] 41612/74 Heading C3H Peptides of Formula (I) wherein X is Ala or Leu, and the non-toxic salts thereof (hydrocholoride, hydrobromide, sulphate, phosphate, maleate, acetate, citrate, benzoate, succinate, malate or ascorbate). Derivatives of (I) of Formula (II) wherein N<SP>9</SP> represents side chain nitrogen atoms of Arg, R is NH 2 , OH, O-(lower)alkyl ("lower" being C 1-6 ), O-benzyl, R<SP>1</SP> is a protecting group for the N<SP>8</SP>, N<SP>#</SP>, N<SP>#1</SP> atoms of Arg, and is nitro, tosyl, benzyloxycarbonyl or adamantyloxycarbonyl (if R<SP>1</SP> is nitro or tosyl, protection is on either the N<SP>#</SP> or N<SP>#1</SP> and, if R<SP>1</SP> is benzyloxycarbonyl or adamantyloxycarbonyl, protection is on N<SP>#</SP> and either N<SP>#</SP> or N<SP>#1</SP>); R<SP>2</SP> is a protecting group for the phenolic hydroxyl of Tyr and is acetyl, tosyl, benzoyl, t-butyl, tetrahydropyranyl, trityl, benzyl, 2,4-dichlorobenzyl or benzyloxycarbonyl; R<SP>3</SP> is a protecting group for the alcoholic hydroxyl of Ser and is one specified for R<SP>2</SP>; R<SP>4</SP> is an aminoprotecting group or hydrogen; wherein R<SP>1</SP>, R<SP>2</SP> or R<SP>3</SP> may also be hydrogen, with the proviso that at least one of R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> is a protecting group and the non-toxic salts thereof. Derivatives of (II) of Formula (III) wherein R<SP>5</SP> is R<SP>4</SP>-(Pry)Glu, an α-aminoprotecting group or hydrogen; and A represents one of Preferred resins are benzhydrilamine, chloromethylated or hydroxymethyl styrene resins. The peptides may be prepared by Merrifield synthesis, to yield (III), followed by either (i) a one step cleavage and deprotection to yield (I) or (ii) cleavage to yield (II) followed by deprotection. Step (i) may be effected with hydrogen fluoride using benzhydrilamine resin, and step (ii) ammonolysis using a chloromethylated or hydroxymethyl resin. In the examples, the following peptides were prepared: H-(Pyr)Glu-D-Phe-Trp- Ser(Bzl) - Tyr(Bzl) - D - Ala - Leu- Arg(NO 2 ) - Pro - Gly benzhydrilamine resin; H - (Pyr)Glu - D - Phe - Trp - Ser- Tyr - D - Ala - Leu - Arg - Pro - Gly- NH 2 and acetate; H-(Pyr)Glu-D-Phe- Trp - Ser(Bzl) - Tyr(Bzl) - D - Leu- Leu - Arg(NO 2 ) - Pro - Gly benzhydrilamine resin; H - (Pyr)Glu - D - Phe - Trp- Ser - Tyr - D - Leu - Leu - Arg - Pro- Gly.NH 2 and acetate. Pharmaceutical compositions, for the inhibition of ovulation in female mammals, comprises a peptide of Formula (I) or a non-toxic salt thereof and a pharmaceutically acceptable carrier, said composition may be in unit dosage form.
[GB1458685A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00402958A US3855199A (en) | 1973-10-03 | 1973-10-03 | P-glu-d-phe-t rp-ser-tyr-d-ala-leu-arg-pro-gly-nh2-and intermediates |
| US417983A US3886137A (en) | 1973-11-21 | 1973-11-21 | P-Glu-D-Phe-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-Gly-NH{HD 2 {B and intermediates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE40930L true IE40930L (en) | 1975-04-03 |
| IE40930B1 IE40930B1 (en) | 1979-09-12 |
Family
ID=27018102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2036/74A IE40930B1 (en) | 1973-10-03 | 1974-10-01 | Decapeptides |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5059367A (en) |
| CA (1) | CA1022546A (en) |
| CH (1) | CH605676A5 (en) |
| DE (1) | DE2447097A1 (en) |
| FR (1) | FR2247254B1 (en) |
| GB (1) | GB1458685A (en) |
| IE (1) | IE40930B1 (en) |
| NL (1) | NL7413081A (en) |
| NZ (1) | NZ175566A (en) |
| PH (1) | PH11571A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4409208A (en) * | 1980-04-15 | 1983-10-11 | The Salk Institute For Biological Studies | GnRH antagonists |
| DE3842010A1 (en) * | 1988-12-14 | 1990-06-21 | Hoechst Ag | COMPETITIVE GONADOLIBERINE ANTAGONISTS |
-
1974
- 1974-09-20 PH PH16314A patent/PH11571A/en unknown
- 1974-09-23 CA CA209,974A patent/CA1022546A/en not_active Expired
- 1974-09-25 GB GB4161274A patent/GB1458685A/en not_active Expired
- 1974-10-01 IE IE2036/74A patent/IE40930B1/en unknown
- 1974-10-01 NZ NZ175566A patent/NZ175566A/en unknown
- 1974-10-02 CH CH1327474A patent/CH605676A5/xx not_active IP Right Cessation
- 1974-10-02 JP JP49114274A patent/JPS5059367A/ja active Pending
- 1974-10-02 DE DE19742447097 patent/DE2447097A1/en not_active Withdrawn
- 1974-10-02 FR FR7433242A patent/FR2247254B1/fr not_active Expired
- 1974-10-03 NL NL7413081A patent/NL7413081A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1022546A (en) | 1977-12-13 |
| DE2447097A1 (en) | 1975-04-10 |
| PH11571A (en) | 1978-03-31 |
| CH605676A5 (en) | 1978-10-13 |
| NZ175566A (en) | 1978-06-20 |
| JPS5059367A (en) | 1975-05-22 |
| GB1458685A (en) | 1976-12-15 |
| NL7413081A (en) | 1975-04-07 |
| FR2247254A1 (en) | 1975-05-09 |
| IE40930B1 (en) | 1979-09-12 |
| AU7352074A (en) | 1976-03-25 |
| FR2247254B1 (en) | 1980-01-11 |
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