EA022476B1 - Индолсульфонильные защищенные соединения и способ их получения - Google Patents
Индолсульфонильные защищенные соединения и способ их получения Download PDFInfo
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- EA022476B1 EA022476B1 EA201001738A EA201001738A EA022476B1 EA 022476 B1 EA022476 B1 EA 022476B1 EA 201001738 A EA201001738 A EA 201001738A EA 201001738 A EA201001738 A EA 201001738A EA 022476 B1 EA022476 B1 EA 022476B1
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- Eurasian Patent Office
- Prior art keywords
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 142
- 238000000034 method Methods 0.000 title claims abstract description 40
- -1 Indolesulfonyl Chemical group 0.000 title claims description 18
- 230000008569 process Effects 0.000 title abstract description 4
- 238000002360 preparation method Methods 0.000 title description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 44
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 99
- 239000001257 hydrogen Substances 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 229920005989 resin Polymers 0.000 claims description 55
- 239000011347 resin Substances 0.000 claims description 55
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 150000001413 amino acids Chemical class 0.000 claims description 27
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 25
- 125000000539 amino acid group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 239000004475 Arginine Substances 0.000 claims description 14
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 14
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 14
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 14
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 239000012634 fragment Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
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- 108010038807 Oligopeptides Proteins 0.000 claims description 9
- QUOGESRFPZDMMT-UHFFFAOYSA-N L-Homoarginine Natural products OC(=O)C(N)CCCCNC(N)=N QUOGESRFPZDMMT-UHFFFAOYSA-N 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 230000010933 acylation Effects 0.000 claims description 7
- 238000005917 acylation reaction Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
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- 150000002357 guanidines Chemical class 0.000 claims 1
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- 125000006239 protecting group Chemical group 0.000 abstract description 20
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- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 abstract description 3
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- 239000000243 solution Substances 0.000 description 31
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 13
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 11
- 238000005859 coupling reaction Methods 0.000 description 11
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- SMFFZOQLHYIRDA-UHFFFAOYSA-N 3,4-dimethoxyphenol Chemical compound COC1=CC=C(O)C=C1OC SMFFZOQLHYIRDA-UHFFFAOYSA-N 0.000 description 6
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- 241000283707 Capra Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- IFPQOXNWLSRZKX-UHFFFAOYSA-N 2-amino-4-(diaminomethylideneamino)butanoic acid Chemical group OC(=O)C(N)CCN=C(N)N IFPQOXNWLSRZKX-UHFFFAOYSA-N 0.000 description 4
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- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- DWKPPFQULDPWHX-VKHMYHEASA-N l-alanyl ester Chemical compound COC(=O)[C@H](C)N DWKPPFQULDPWHX-VKHMYHEASA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000036185 rubor Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003954 δ-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- 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)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08008418 | 2008-05-05 | ||
| US9570908P | 2008-09-10 | 2008-09-10 | |
| PCT/EP2009/003210 WO2009135645A1 (en) | 2008-05-05 | 2009-05-05 | Indolesulfonyl protecting groups for protection of guanidino and amino groups |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201001738A1 EA201001738A1 (ru) | 2011-06-30 |
| EA022476B1 true EA022476B1 (ru) | 2016-01-29 |
Family
ID=39772857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201001738A EA022476B1 (ru) | 2008-05-05 | 2009-05-05 | Индолсульфонильные защищенные соединения и способ их получения |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8431720B2 (enExample) |
| EP (2) | EP2420489B1 (enExample) |
| JP (2) | JP5567004B2 (enExample) |
| KR (2) | KR101521400B1 (enExample) |
| CN (1) | CN102026971B (enExample) |
| AU (1) | AU2009243730B2 (enExample) |
| BR (1) | BRPI0912355A2 (enExample) |
| CA (1) | CA2721644C (enExample) |
| CO (1) | CO6390068A2 (enExample) |
| DK (1) | DK2420489T3 (enExample) |
| EA (1) | EA022476B1 (enExample) |
| ES (1) | ES2477590T3 (enExample) |
| IL (1) | IL208930A (enExample) |
| MX (1) | MX2010012113A (enExample) |
| WO (1) | WO2009135645A1 (enExample) |
| ZA (1) | ZA201007614B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103626996B (zh) * | 2013-11-29 | 2016-04-27 | 沈阳药科大学 | 胍基化的含二硫键聚氨基胺类聚合物及其制备和应用 |
| EP3305780A1 (en) | 2016-10-05 | 2018-04-11 | Lonza Ltd | Method for the preparation of h-arg(mis)-oh |
| WO2018064829A1 (en) * | 2016-10-09 | 2018-04-12 | Polypeptide Laboratories Holding (Ppl) Ab | Method for the preparation of h-arg (mis) -oh |
| EP3315490A1 (en) | 2016-10-31 | 2018-05-02 | Polypeptide Laboratories Holding (PPL) AB | Method for the preparation of h-arg(mis)-oh |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001057045A1 (de) * | 2000-02-02 | 2001-08-09 | Boehringer Ingelheim Pharma Kg | Neue positive allosterische ampa-rezeptor modulatoren (paarm), verfahren zu deren herstellung und deren verwendung als arzneimittel |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1501826B1 (en) | 2002-02-01 | 2006-09-27 | F. Hoffman-la Roche AG | Substituted indoles as alpha-1 agonists |
| CN100453537C (zh) * | 2004-05-08 | 2009-01-21 | 上海依福瑞实业有限公司 | 一种双保护氨基酸的制备方法 |
| US8585885B2 (en) * | 2007-08-28 | 2013-11-19 | Rohm And Haas Electronic Materials Llc | Electrochemically deposited indium composites |
-
2009
- 2009-05-05 KR KR1020147010770A patent/KR101521400B1/ko not_active Expired - Fee Related
- 2009-05-05 BR BRPI0912355-5A patent/BRPI0912355A2/pt not_active IP Right Cessation
- 2009-05-05 JP JP2011507824A patent/JP5567004B2/ja not_active Expired - Fee Related
- 2009-05-05 EA EA201001738A patent/EA022476B1/ru not_active IP Right Cessation
- 2009-05-05 EP EP11007876.3A patent/EP2420489B1/en not_active Not-in-force
- 2009-05-05 CN CN200980118481.3A patent/CN102026971B/zh not_active Expired - Fee Related
- 2009-05-05 EP EP09741864A patent/EP2280942A1/en not_active Withdrawn
- 2009-05-05 AU AU2009243730A patent/AU2009243730B2/en not_active Ceased
- 2009-05-05 CA CA2721644A patent/CA2721644C/en active Active
- 2009-05-05 US US12/990,934 patent/US8431720B2/en not_active Expired - Fee Related
- 2009-05-05 ES ES11007876.3T patent/ES2477590T3/es active Active
- 2009-05-05 WO PCT/EP2009/003210 patent/WO2009135645A1/en not_active Ceased
- 2009-05-05 MX MX2010012113A patent/MX2010012113A/es active IP Right Grant
- 2009-05-05 DK DK11007876.3T patent/DK2420489T3/da active
- 2009-05-05 KR KR1020107026990A patent/KR101493554B1/ko not_active Expired - Fee Related
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2010
- 2010-10-25 ZA ZA2010/07614A patent/ZA201007614B/en unknown
- 2010-10-25 IL IL208930A patent/IL208930A/en active IP Right Grant
- 2010-11-03 CO CO10136369A patent/CO6390068A2/es active IP Right Grant
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2014
- 2014-04-28 JP JP2014092764A patent/JP5985534B2/ja not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001057045A1 (de) * | 2000-02-02 | 2001-08-09 | Boehringer Ingelheim Pharma Kg | Neue positive allosterische ampa-rezeptor modulatoren (paarm), verfahren zu deren herstellung und deren verwendung als arzneimittel |
Non-Patent Citations (1)
| Title |
|---|
| CARPINO L.A. ET AL.: "THE 2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-S ULFONYL GROUP (PBF) AS ARGININE SIDE CHAIN PROTECTANT" TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, vol. 34, no. 49, 1 January 1993 (1993-01-01), pages 7829-7832, XP000943537 ISSN: 0040-4039 the whole document * |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101521400B1 (ko) | 2015-05-18 |
| JP5985534B2 (ja) | 2016-09-06 |
| AU2009243730B2 (en) | 2013-07-18 |
| ES2477590T3 (es) | 2014-07-17 |
| EP2280942A1 (en) | 2011-02-09 |
| JP5567004B2 (ja) | 2014-08-06 |
| US20110060125A1 (en) | 2011-03-10 |
| EP2420489B1 (en) | 2014-04-23 |
| MX2010012113A (es) | 2010-12-01 |
| AU2009243730A1 (en) | 2009-11-12 |
| CN102026971B (zh) | 2014-10-29 |
| CA2721644A1 (en) | 2009-11-12 |
| JP2011519884A (ja) | 2011-07-14 |
| IL208930A (en) | 2014-07-31 |
| KR20140061548A (ko) | 2014-05-21 |
| IL208930A0 (en) | 2011-01-31 |
| HK1154860A1 (en) | 2012-05-04 |
| CO6390068A2 (es) | 2012-02-29 |
| JP2014193872A (ja) | 2014-10-09 |
| CN102026971A (zh) | 2011-04-20 |
| CA2721644C (en) | 2013-10-15 |
| ZA201007614B (en) | 2011-07-27 |
| EP2420489A1 (en) | 2012-02-22 |
| KR20110014167A (ko) | 2011-02-10 |
| EA201001738A1 (ru) | 2011-06-30 |
| WO2009135645A1 (en) | 2009-11-12 |
| DK2420489T3 (da) | 2014-07-21 |
| US8431720B2 (en) | 2013-04-30 |
| KR101493554B1 (ko) | 2015-02-16 |
| BRPI0912355A2 (pt) | 2015-07-28 |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
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