CS197268B2 - Process for preparing l-pyroglutamyl-l-histidyl-3-alkylprolinamides - Google Patents
Process for preparing l-pyroglutamyl-l-histidyl-3-alkylprolinamides Download PDFInfo
- Publication number
- CS197268B2 CS197268B2 CS761513A CS151376A CS197268B2 CS 197268 B2 CS197268 B2 CS 197268B2 CS 761513 A CS761513 A CS 761513A CS 151376 A CS151376 A CS 151376A CS 197268 B2 CS197268 B2 CS 197268B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- pyroglutamyl
- trans
- hydrogen
- histidyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 238000007259 addition reaction Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 claims description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- VQJMAIZOEPPELO-KYGIZGOZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-(2-hydroxy-5-methylhexan-2-yl)-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol hydrochloride Chemical compound Cl.CO[C@]12CC[C@@]3(C[C@@H]1C(C)(O)CCC(C)C)[C@H]1Cc4ccc(O)c5O[C@@H]2[C@]3(CCN1CC1CC1)c45 VQJMAIZOEPPELO-KYGIZGOZSA-N 0.000 abstract 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- WGSPBTQXEQZIMR-UHFFFAOYSA-N diethyl 3,3-dimethylpyrrolidine-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)NCCC1(C)C WGSPBTQXEQZIMR-UHFFFAOYSA-N 0.000 description 1
- PWMIGCQCGGMVRU-UHFFFAOYSA-N diethyl 3-ethyl-1,3-dihydropyrrole-2,2-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)NC=CC1CC PWMIGCQCGGMVRU-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 210000001883 posterior pituitary gland Anatomy 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- LJFPGBIHDPZHIN-UHFFFAOYSA-N tert-butyl (2,4,5-trichlorophenyl) carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC(Cl)=C(Cl)C=C1Cl LJFPGBIHDPZHIN-UHFFFAOYSA-N 0.000 description 1
- LBVZYIYEWDLJMP-UHFFFAOYSA-N tert-butyl 2-carbamoyl-3,3-dimethylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C)(C)C1C(N)=O LBVZYIYEWDLJMP-UHFFFAOYSA-N 0.000 description 1
- 229960000874 thyrotropin Drugs 0.000 description 1
- 230000001748 thyrotropin Effects 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- 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
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
- C07K5/0825—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Glp-amino acid; Derivatives thereof
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10144/75A GB1523598A (en) | 1975-03-08 | 1975-03-08 | Tripeptides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS197268B2 true CS197268B2 (en) | 1980-04-30 |
Family
ID=9962321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS761513A CS197268B2 (en) | 1975-03-08 | 1976-03-08 | Process for preparing l-pyroglutamyl-l-histidyl-3-alkylprolinamides |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4060603A (es) |
| JP (1) | JPS5940144B2 (es) |
| AR (1) | AR208361A1 (es) |
| AT (1) | AT352918B (es) |
| BE (1) | BE839187A (es) |
| CA (1) | CA1059994A (es) |
| CH (1) | CH608484A5 (es) |
| CS (1) | CS197268B2 (es) |
| DE (1) | DE2609154C2 (es) |
| DK (1) | DK97376A (es) |
| EG (1) | EG13624A (es) |
| ES (1) | ES445763A1 (es) |
| FI (1) | FI62823C (es) |
| FR (1) | FR2303559A1 (es) |
| GB (1) | GB1523598A (es) |
| GR (1) | GR59891B (es) |
| HU (1) | HU175652B (es) |
| IE (1) | IE42784B1 (es) |
| IL (1) | IL49122A (es) |
| LU (1) | LU74483A1 (es) |
| MX (1) | MX3055E (es) |
| NL (1) | NL7602257A (es) |
| NO (1) | NO144604C (es) |
| OA (1) | OA05260A (es) |
| PH (1) | PH11727A (es) |
| PL (1) | PL101401B1 (es) |
| PT (1) | PT64853B (es) |
| SE (1) | SE411671B (es) |
| SU (1) | SU619101A3 (es) |
| YU (1) | YU58176A (es) |
| ZA (1) | ZA761062B (es) |
| ZM (1) | ZM2576A1 (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5920647B2 (ja) * | 1976-10-01 | 1984-05-15 | 武田薬品工業株式会社 | 注射剤 |
| US4182856A (en) * | 1978-04-25 | 1980-01-08 | Miles Laboratories, Inc. | Reagents for use in binding assays to determine diphenylhydantoin |
| CA1256650A (en) * | 1983-03-25 | 1989-06-27 | Toshinari Tamura | Process of producing 2-azetidinone-4-substituted compounds, and medicaments containing the compounds |
| JPS59195038U (ja) * | 1983-06-14 | 1984-12-25 | 株式会社村上開明堂 | バツクミラ− |
| JPS59195037U (ja) * | 1983-06-14 | 1984-12-25 | 株式会社村上開明堂 | バツクミラ− |
| GB2146026A (en) * | 1983-09-07 | 1985-04-11 | Tanabe Seiyaku Co | Peptides and process for preparing the same |
| FR2622581B1 (fr) * | 1987-11-03 | 1990-02-16 | Inorgan Sa Rech Develop Pharm | Nouveaux derives de l-proline, leur preparation et leurs applications biologiques |
| FR2649110B1 (fr) * | 1989-06-29 | 1994-10-21 | Adir | Nouveaux derives peptidiques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| DK437289D0 (da) * | 1989-09-04 | 1989-09-04 | Hans Bundgaard | Prodrug derivatives of thyrotropin-releasing hormone (trh) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2343035C2 (de) * | 1973-08-25 | 1982-04-01 | Hoechst Ag, 6000 Frankfurt | Pyroglutamyl-histidyl-prolinamide, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US3959248A (en) * | 1974-04-03 | 1976-05-25 | Merck & Co., Inc. | Analogs of thyrotropin-releasing hormone |
-
1975
- 1975-03-08 GB GB10144/75A patent/GB1523598A/en not_active Expired
-
1976
- 1976-01-01 AR AR262475A patent/AR208361A1/es active
- 1976-02-20 CA CA246,250A patent/CA1059994A/en not_active Expired
- 1976-02-20 US US05/659,913 patent/US4060603A/en not_active Expired - Lifetime
- 1976-02-23 SE SE7602165A patent/SE411671B/xx not_active IP Right Cessation
- 1976-02-24 ZA ZA761062A patent/ZA761062B/xx unknown
- 1976-02-27 PT PT64853A patent/PT64853B/pt unknown
- 1976-02-29 IL IL49122A patent/IL49122A/xx unknown
- 1976-03-02 FI FI760538A patent/FI62823C/fi not_active IP Right Cessation
- 1976-03-02 PH PH18163A patent/PH11727A/en unknown
- 1976-03-03 GR GR50233A patent/GR59891B/el unknown
- 1976-03-03 ZM ZM25/76A patent/ZM2576A1/xx unknown
- 1976-03-03 JP JP51023063A patent/JPS5940144B2/ja not_active Expired
- 1976-03-04 NO NO760741A patent/NO144604C/no unknown
- 1976-03-04 ES ES445763A patent/ES445763A1/es not_active Expired
- 1976-03-04 BE BE164854A patent/BE839187A/xx not_active IP Right Cessation
- 1976-03-04 NL NL7602257A patent/NL7602257A/xx not_active Application Discontinuation
- 1976-03-05 DE DE2609154A patent/DE2609154C2/de not_active Expired
- 1976-03-05 OA OA55754A patent/OA05260A/xx unknown
- 1976-03-05 DK DK97376*#A patent/DK97376A/da not_active Application Discontinuation
- 1976-03-05 SU SU762331353A patent/SU619101A3/ru active
- 1976-03-05 PL PL1976187742A patent/PL101401B1/pl unknown
- 1976-03-05 CH CH282376A patent/CH608484A5/xx not_active IP Right Cessation
- 1976-03-05 FR FR7606369A patent/FR2303559A1/fr active Granted
- 1976-03-05 LU LU74483A patent/LU74483A1/xx unknown
- 1976-03-08 CS CS761513A patent/CS197268B2/cs unknown
- 1976-03-08 AT AT169776A patent/AT352918B/de not_active IP Right Cessation
- 1976-03-08 MX MX000050U patent/MX3055E/es unknown
- 1976-03-08 IE IE477/76A patent/IE42784B1/en unknown
- 1976-03-08 YU YU00581/76A patent/YU58176A/xx unknown
- 1976-03-08 HU HU76RE580A patent/HU175652B/hu unknown
- 1976-03-09 EG EG139/76A patent/EG13624A/xx active
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