NO844123L - Fremgangsmaate for fremstilling av nonapeptider og dodekopeptider - Google Patents
Fremgangsmaate for fremstilling av nonapeptider og dodekopeptiderInfo
- Publication number
- NO844123L NO844123L NO844123A NO844123A NO844123L NO 844123 L NO844123 L NO 844123L NO 844123 A NO844123 A NO 844123A NO 844123 A NO844123 A NO 844123A NO 844123 L NO844123 L NO 844123L
- Authority
- NO
- Norway
- Prior art keywords
- glu
- compound
- acyl
- pharmaceutically acceptable
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims description 43
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 40
- 229920005989 resin Polymers 0.000 claims description 29
- 239000011347 resin Substances 0.000 claims description 29
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 23
- 229920001184 polypeptide Polymers 0.000 claims description 21
- -1 alkyl carboxylic acid Chemical class 0.000 claims description 14
- 231100000252 nontoxic Toxicity 0.000 claims description 10
- 230000003000 nontoxic effect Effects 0.000 claims description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Chemical group OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 6
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical group OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 5
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000007790 solid phase Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 108010077805 Bacterial Proteins Proteins 0.000 claims description 2
- 108700005078 Synthetic Genes Proteins 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
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- 108010038807 Oligopeptides Proteins 0.000 claims 1
- ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 claims 1
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
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- 102000004169 proteins and genes Human genes 0.000 claims 1
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
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- MJIBOYFUEIDNPI-HBNMXAOGSA-L zinc 5-[2,3-dihydroxy-5-[(2R,3R,4S,5R,6S)-4,5,6-tris[[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl]oxy]-2-[[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl]oxymethyl]oxan-3-yl]oxycarbonylphenoxy]carbonyl-3-hydroxybenzene-1,2-diolate Chemical class [Zn++].Oc1cc(cc(O)c1O)C(=O)Oc1cc(cc(O)c1O)C(=O)OC[C@H]1O[C@@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@@H]1OC(=O)c1cc(O)c(O)c(OC(=O)c2cc(O)c([O-])c([O-])c2)c1 MJIBOYFUEIDNPI-HBNMXAOGSA-L 0.000 description 4
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- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
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- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
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- 238000005119 centrifugation Methods 0.000 description 1
- RICFWCXESOWLSS-UHFFFAOYSA-M cesium;2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate Chemical compound [Cs+].CC(C)(C)OC(=O)NCC([O-])=O RICFWCXESOWLSS-UHFFFAOYSA-M 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
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- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
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- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical group C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
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- 235000019253 formic acid Nutrition 0.000 description 1
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- 235000012208 gluconic acid Nutrition 0.000 description 1
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- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000367 immunologic factor Substances 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000031942 natural killer cell mediated cytotoxicity Effects 0.000 description 1
- 238000011587 new zealand white rabbit Methods 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000012071 phase Substances 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
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 108020001775 protein parts Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 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
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
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- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 231100000161 signs of toxicity Toxicity 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
- 239000011734 sodium Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 238000012360 testing method Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 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
- 229940005605 valeric acid Drugs 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/06—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by azeotropic distillation
-
- 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
- C07K14/52—Cytokines; Lymphokines; Interferons
- C07K14/555—Interferons [IFN]
- C07K14/57—IFN-gamma
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/542,632 US4473555A (en) | 1983-10-17 | 1983-10-17 | Nona- and dodecapeptides for augmenting natural killer cell activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO844123L true NO844123L (no) | 1985-04-18 |
Family
ID=24164663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO844123A NO844123L (no) | 1983-10-17 | 1984-10-16 | Fremgangsmaate for fremstilling av nonapeptider og dodekopeptider |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4473555A (fi) |
| EP (1) | EP0138616A3 (fi) |
| JP (1) | JPS6087299A (fi) |
| KR (1) | KR850003416A (fi) |
| AU (1) | AU3428784A (fi) |
| DK (1) | DK495484A (fi) |
| ES (1) | ES8605538A1 (fi) |
| FI (1) | FI844068L (fi) |
| HU (1) | HUT35695A (fi) |
| IL (1) | IL73256A0 (fi) |
| NO (1) | NO844123L (fi) |
| PL (1) | PL250044A1 (fi) |
| ZA (1) | ZA848070B (fi) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5019384A (en) * | 1986-06-30 | 1991-05-28 | Massachusetts Institute Of Technology | Immunonodulating compositions and their use |
| JP2633881B2 (ja) | 1986-06-30 | 1997-07-23 | マサチューセッツ インスティテュート オブ テクノロジー | 免疫調節組成物及びそれらの使用 |
| US5457038A (en) * | 1988-11-10 | 1995-10-10 | Genetics Institute, Inc. | Natural killer stimulatory factor |
| WO1990005147A1 (en) * | 1988-11-10 | 1990-05-17 | Genetics Institute, Inc. | Natural killer stimulatory factor |
| US5811523A (en) | 1988-11-10 | 1998-09-22 | Trinchieri; Giorgio | Antibodies to natural killer stimulatory factor |
| IT1231727B (it) * | 1989-08-11 | 1991-12-21 | Enrico Savoldi | Peptidi utili per la determinazione e la purificazione di anticorpi anti gamma interferone. |
| CA2042027A1 (en) * | 1989-09-15 | 1991-03-16 | Arthur E. Bogden | Treatment of colon cancer |
| US6683046B1 (en) | 1989-12-22 | 2004-01-27 | Hoffmann-La Roche Inc. | Purification and characterization of cytotoxic lymphocyte maturation factor and monoclonal antibodies thereto |
| US7026456B1 (en) | 1998-01-23 | 2006-04-11 | Hoffman-La Roche, Inc. | Antibodies against human IL-12 |
| GB0211849D0 (en) * | 2002-05-23 | 2002-07-03 | Mok Kenneth H | Improvments to retro-inverso isomers |
| EP4162925A1 (en) * | 2020-06-08 | 2023-04-12 | Ninebiopharm Co., Ltd. | Composition comprising regentide-034 and regentide-041 for skin care or wrinkle reduction |
-
1983
- 1983-10-17 US US06/542,632 patent/US4473555A/en not_active Expired - Fee Related
-
1984
- 1984-08-30 JP JP59181626A patent/JPS6087299A/ja active Pending
- 1984-10-16 IL IL73256A patent/IL73256A0/xx unknown
- 1984-10-16 KR KR1019840006412A patent/KR850003416A/ko not_active Application Discontinuation
- 1984-10-16 EP EP84307090A patent/EP0138616A3/en not_active Withdrawn
- 1984-10-16 ES ES536795A patent/ES8605538A1/es not_active Expired
- 1984-10-16 ZA ZA848070A patent/ZA848070B/xx unknown
- 1984-10-16 FI FI844068A patent/FI844068L/fi not_active Application Discontinuation
- 1984-10-16 AU AU34287/84A patent/AU3428784A/en not_active Abandoned
- 1984-10-16 DK DK495484A patent/DK495484A/da not_active Application Discontinuation
- 1984-10-16 HU HU843860A patent/HUT35695A/hu unknown
- 1984-10-16 NO NO844123A patent/NO844123L/no unknown
- 1984-10-16 PL PL25004484A patent/PL250044A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL73256A0 (en) | 1985-01-31 |
| ES8605538A1 (es) | 1986-04-01 |
| PL250044A1 (en) | 1985-06-04 |
| US4473555A (en) | 1984-09-25 |
| EP0138616A2 (en) | 1985-04-24 |
| AU3428784A (en) | 1985-04-26 |
| ES536795A0 (es) | 1986-04-01 |
| DK495484A (da) | 1985-04-18 |
| EP0138616A3 (en) | 1987-06-16 |
| FI844068L (fi) | 1985-04-18 |
| HUT35695A (en) | 1985-07-29 |
| FI844068A0 (fi) | 1984-10-16 |
| ZA848070B (en) | 1986-05-28 |
| JPS6087299A (ja) | 1985-05-16 |
| DK495484D0 (da) | 1984-10-16 |
| KR850003416A (ko) | 1985-06-17 |
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