KR860002194B1 - A-21978c 사이클릭 펩타이드 유도체의 제조방법 - Google Patents

A-21978c 사이클릭 펩타이드 유도체의 제조방법 Download PDF

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Publication number: KR860002194B1
Authority: KR; South Korea
Prior art keywords: group; hydrogen; general formula; amino protecting; alkanoyl
Prior art date: 1982-05-21
Legal status (The legal status 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 status listed.): Expired

Application number

KR1019830002224A

Other languages

English (en)

Korean (ko)

Other versions

KR840005078A (ko

Inventor

죤 아보트 버나드

데보느 마뉴엘

슈이찌 후꾸다 데비드

Original Assignee

일라이 릴리 앤드 캄파니

아더 알. 웨일

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.)

1982-05-21

Filing date

1983-05-19

Publication date

1986-12-30

1983-05-19 Application filed by 일라이 릴리 앤드 캄파니, 아더 알. 웨일 filed Critical 일라이 릴리 앤드 캄파니

1984-11-03 Publication of KR840005078A publication Critical patent/KR840005078A/ko

1986-12-30 Application granted granted Critical

1986-12-30 Publication of KR860002194B1 publication Critical patent/KR860002194B1/ko

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 47
108090000765 processed proteins & peptides Proteins 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title description 28
230000008569 process Effects 0.000 title description 7
102000004196 processed proteins & peptides Human genes 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 73
-1 8-methyldecanoyl Chemical group 0.000 claims description 61
229910052739 hydrogen Inorganic materials 0.000 claims description 43
239000001257 hydrogen Substances 0.000 claims description 42
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
125000006239 protecting group Chemical group 0.000 claims description 38
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
108010069514 Cyclic Peptides Proteins 0.000 claims description 23
102000001189 Cyclic Peptides Human genes 0.000 claims description 23
125000002252 acyl group Chemical group 0.000 claims description 22
150000002431 hydrogen Chemical class 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 11
230000002829 reductive effect Effects 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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238000010521 absorption reaction Methods 0.000 description 6
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239000000758 substrate Substances 0.000 description 6
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
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NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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150000001412 amines Chemical class 0.000 description 3
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229940043376 ammonium acetate Drugs 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
150000001805 chlorine compounds Chemical class 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
125000004122 cyclic group Chemical group 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
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230000000670 limiting effect Effects 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 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
229940098779 methanesulfonic acid Drugs 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
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150000007522 mineralic acids Chemical class 0.000 description 1
LULXBAGMGMJJRW-UHFFFAOYSA-N n,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)CC(=O)N[Si](C)(C)C LULXBAGMGMJJRW-UHFFFAOYSA-N 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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239000001301 oxygen Substances 0.000 description 1
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WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 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
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UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
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239000012048 reactive intermediate Substances 0.000 description 1
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229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
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239000008117 stearic acid Substances 0.000 description 1
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125000001424 substituent group Chemical group 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000048 toxicity data Toxicity 0.000 description 1
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238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Classifications

- 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

Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

KR1019830002224A 1982-05-21 1983-05-19 A-21978c 사이클릭 펩타이드 유도체의 제조방법 Expired KR860002194B1 (ko)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US38201282A	1982-05-21	1982-05-21
US382012		1982-05-21

Publications (2)

Publication Number	Publication Date
KR840005078A KR840005078A (ko)	1984-11-03
KR860002194B1 true KR860002194B1 (ko)	1986-12-30

Family

ID=23507203

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
KR1019830002224A Expired KR860002194B1 (ko)	1982-05-21	1983-05-19	A-21978c 사이클릭 펩타이드 유도체의 제조방법

Country Status (15)

Country	Link
KR (1)	KR860002194B1 (fr)
AT (1)	AT402299B (fr)
BG (1)	BG40657A3 (fr)
CA (1)	CA1216579A (fr)
CS (1)	CS257766B2 (fr)
DD (1)	DD210257A5 (fr)
DK (1)	DK221183A (fr)
EG (1)	EG16044A (fr)
ES (1)	ES8502081A1 (fr)
FI (1)	FI79118C (fr)
GR (1)	GR78851B (fr)
HU (1)	HU193039B (fr)
PL (1)	PL142112B1 (fr)
PT (1)	PT76703B (fr)
RO (1)	RO86722B (fr)

1983
- 1983-05-13 CA CA000428101A patent/CA1216579A/fr not_active Expired
- 1983-05-16 AT AT0178583A patent/AT402299B/de not_active IP Right Cessation
- 1983-05-16 PT PT76703A patent/PT76703B/pt unknown
- 1983-05-16 RO RO110958A patent/RO86722B/ro unknown
- 1983-05-18 EG EG298/83A patent/EG16044A/xx active
- 1983-05-18 FI FI831756A patent/FI79118C/fi not_active IP Right Cessation
- 1983-05-18 DK DK221183A patent/DK221183A/da not_active Application Discontinuation
- 1983-05-19 BG BG061022A patent/BG40657A3/xx unknown
- 1983-05-19 ES ES522562A patent/ES8502081A1/es not_active Expired
- 1983-05-19 KR KR1019830002224A patent/KR860002194B1/ko not_active Expired
- 1983-05-19 GR GR78851A patent/GR78851B/el unknown
- 1983-05-20 CS CS833607A patent/CS257766B2/cs unknown
- 1983-05-20 DD DD83251128A patent/DD210257A5/de unknown
- 1983-05-20 PL PL1983242098A patent/PL142112B1/pl unknown
- 1983-05-20 HU HU831796A patent/HU193039B/hu unknown

Also Published As

Publication number	Publication date
ES522562A0 (es)	1984-12-16
PL242098A1 (en)	1984-07-02
EG16044A (en)	1991-03-30
RO86722B (ro)	1985-05-01
PT76703A (en)	1983-06-01
AT402299B (de)	1997-03-25
PL142112B1 (en)	1987-09-30
HU193039B (en)	1987-08-28
BG40657A3 (en)	1987-01-15
PT76703B (pt)	1986-03-27
DD210257A5 (de)	1984-06-06
DK221183A (da)	1983-11-22
CS257766B2 (en)	1988-06-15
FI79118C (fi)	1989-11-10
ATA178583A (de)	1996-08-15
RO86722A (fr)	1985-04-17
FI831756L (fi)	1983-11-22
KR840005078A (ko)	1984-11-03
FI79118B (fi)	1989-07-31
DK221183D0 (da)	1983-05-18
ES8502081A1 (es)	1984-12-16
GR78851B (fr)	1984-10-02
CS360783A2 (en)	1987-09-17
CA1216579A (fr)	1987-01-13
FI831756A0 (fi)	1983-05-18

Publication	Publication Date	Title
US4482487A (en)	1984-11-13	A-21978C cyclic peptides
US4524135A (en)	1985-06-18	A-21978C cyclic peptides
US5039789A (en)	1991-08-13	A54145 cyclic peptides
USRE32311E (en)	1986-12-16	Derivatives of A-21978C cyclic peptides
USRE32310E (en)	1986-12-16	Derivatives of A-21978C cyclic peptides
KR860002185B1 (ko)	1986-12-24	A-21978c 사이클릭 펩티드 유도체의 제조방법
US5028590A (en)	1991-07-02	Derivatives of A54145 cyclic peptides
EP0095295B1 (fr)	1987-01-14	Dérivés de peptides cycliques
KR0139628B1 (ko)	1998-07-01	항생물질 머사시딘, 이의 제조방법 및 이를 함유하는 약제
EP0031221B1 (fr)	1983-03-02	Noyaux de peptides cycliques
KR100482402B1 (ko)	2005-08-31	액타가르딘과관련된신규랜티바이오틱,이의제조방법및이를포함하는약제학적조성물
KR860002193B1 (ko)	1986-12-30	A-21978c 사이클릭 펩타이드 유도체의 제조방법
EP0337731B1 (fr)	1996-01-31	Antibiotiques peptidiques
EP0005956A1 (fr)	1979-12-12	Antibiotiques A-38533, leur préparation, formulations les contenant et microorganisme employé à leur production
KR860002194B1 (ko)	1986-12-30	A-21978c 사이클릭 펩타이드 유도체의 제조방법
KR100221687B1 (ko)	1999-10-01	항생제 발히마이신, 이의 제조방법 및 이를 포함하는 약제
KR860001285B1 (ko)	1986-09-05	A-21978c 사이클릭 펩타이드 유도체의 제조 방법
EP0825194A2 (fr)	1998-02-25	Dérivé amide d'amythiamicin
US6642391B2 (en)	2003-11-04	Amycomycin, a process for its production and its use as a pharmaceutical

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