KR840000488A - 프롤린 유도체의 제법 - Google Patents
프롤린 유도체의 제법 Download PDFInfo
- Publication number
- KR840000488A KR840000488A KR1019820002740A KR820002740A KR840000488A KR 840000488 A KR840000488 A KR 840000488A KR 1019820002740 A KR1019820002740 A KR 1019820002740A KR 820002740 A KR820002740 A KR 820002740A KR 840000488 A KR840000488 A KR 840000488A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- compound represented
- proline
- carbonyl
- producing
- Prior art date
Links
- 150000003147 proline derivatives Chemical class 0.000 title claims 12
- 238000002360 preparation method Methods 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- 239000004471 Glycine Substances 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 150000001718 carbodiimides Chemical class 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- NKLCHDQGUHMCGL-UHFFFAOYSA-N cyclohexylidenemethanone Chemical group O=C=C1CCCCC1 NKLCHDQGUHMCGL-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (22)
- 일반식
-
- (식중 R은 시클로프로판 카르보닐, 시클로헥산 카르보닐 및 아다만탄 카르보닐기로써 된 군으로부터 선택되는 아미노산의 α-아미노기와 결합한 아실기로서 A는 글리신, 잘코신 또는 α-D-아미노산의 잔기이며 그 α-카르보닐기가 유황원자와 티올에스테르 결합을 형성한다)로 나타내는 프롤린 유도체 또는 그의 약학적으로 허용되는 염을 제조함에 있어, 일반식
-
- (식중 A'은 글리신, 잘코신 또는 경우에 있어서 보호기를 갖는 경우가 있는 α-D-아미노산 잔기이며 R은 전기와 같은 뜻을 갖는다)로 나타내는 화합물 또는 그 반응성 유도체와, 일반식
-
- (식중 R'은 수소원자 또는 카르복실기의 보호기를 뜻한다)로 나타내는 화합물 또는 그 반응성 유도체를 불활성 유기용매를 -50~20℃에서 반응시키고 이어서 반응 생성물중에 보호기가 존재할때는 이를 탈리시키고 또한 소망에 따라서 약학적으로 허용되는 염으로 변환함을 특징으로 하는 프롤린 유도체의 제법.
- 제1항에 있어서 일반식(Ⅱ)로 나타내는 화합물의 반응성 유도체가 활성아미드산 할로겐화물, 활성에스테르 또는 혼합산 무수물인 프롤린 유도체의 제법.
- 제1항에 있어 일반식(Ⅱ)로 나타내는 화합물을 카르보디이미드류의 존재하에 일반식(Ⅲ)로 나타내는 화합물 또는 그 반응성 유도체와 반응시킴을 특징으로 하는 프롤린 유도체의 제법.
- 제1항에 있어 일반식(Ⅲ)로 나타내는 화합물의 반응성 유도체가 그 이미노기에 실릴기가 도입된 화합물인 프롤린 유도체의 제법.
- 제1항에 있어 불활성 유기용매가 테트라히드로푸란, 디옥산, 디메틸포름아미드, 헥사메틸포스포트리아미드, 클로로포름, 디클로로메탄 또는 아세트니트릴인 프롤린 유도체의 제법.
- 일반식
-
- (식중 R은 시클로프로판 카르보닐, 시클로헥산 카르보닐 및 아다만탄 카르보닐기로써 된 군으로부터 선택되는 아미노산의 α-아미노기와 결합한 아실기로서 A는 글리신, 질코신 또는 α-D-아미노산의 잔기이며 그 α-카르보닐기가 유황원자와 티올에스테르 결합을 형성한다)로 나타내는 프롤린 유도체 또는 그의 약학적으로 허용되는 염을 제조함에 있어, 일반식
- R-A'-OH (Ⅳ)
- (식중 A'은 글리신, 잘코신 또는 경우에 따라서 보호기를 갖는 경우가 있는 α-D-아미노산 잔기이며 R은 전기와 같은 뜻을 갖는다)로 나타내는 화합물 또는 그 반응성 유도체와 일반식
-
- (식중 R'은 수소원자 또는 카르복실기의 보호기를 뜻한다)로 나타내는 화합물 또는 그 반응성 유도체를 불활성 유기용매중 -50~20℃에서 반응시키고 이어서 반응 생성물중에 보호기가 존재할때는 이를 탈리시키고 또한 소망에 따라서의 약으로서 허용할 수 있는 염으로 변환함을 특징으로 하는 프롤린유도체의 제법.
- 제6항에 있어 일반식(Ⅳ)로 나타내는 화합물의 반응성 유도체가 활성아미드, 산할로겐화물, 활성에스테르 또는 혼합산무수물인 프롤린 유도체의 제법.
- 제6항에 있어 일반식(Ⅳ)로 나타내는 화합물을 카르보디이미드류의 존재하에 일반식(Ⅴ)로 나타내는 화합물과 반응시킴을 특징으로 하는 프롤린 유도체의 제법.
- 제6항에 있어 불활성 유기용매가 테트라히드로푸란, 디옥산, 디메틸포름아미드, 헥사메틸포스포트리아미드, 클로로포름, 디클로로메탄 또는 아세토니트릴인 프롤린 유도체의 제법.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019880015389A KR890000770B1 (ko) | 1981-06-19 | 1988-11-22 | 프롤린 유도체의 제법 |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP56094002A JPS57209270A (en) | 1981-06-19 | 1981-06-19 | Proline derivative |
JP56-94002 | 1981-06-19 | ||
JP56137823A JPS5839661A (ja) | 1981-09-03 | 1981-09-03 | プロリン誘導体の製法 |
JP56-137823 | 1981-09-13 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019880015389A Division KR890000770B1 (ko) | 1981-06-19 | 1988-11-22 | 프롤린 유도체의 제법 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840000488A true KR840000488A (ko) | 1984-02-22 |
KR890000769B1 KR890000769B1 (ko) | 1989-04-05 |
Family
ID=26435270
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR8202740A KR890000769B1 (ko) | 1981-06-19 | 1982-06-19 | 프롤린 유도체의 제법 |
Country Status (19)
Country | Link |
---|---|
KR (1) | KR890000769B1 (ko) |
AT (1) | AT377496B (ko) |
CA (1) | CA1235120A (ko) |
CH (1) | CH651825A5 (ko) |
DE (1) | DE3222779A1 (ko) |
DK (1) | DK156054C (ko) |
ES (2) | ES513277A0 (ko) |
FI (1) | FI75804C (ko) |
FR (1) | FR2508040B1 (ko) |
GB (1) | GB2102412B (ko) |
HU (1) | HU188177B (ko) |
IL (1) | IL65954A (ko) |
IT (1) | IT1157053B (ko) |
MX (2) | MX155724A (ko) |
NL (1) | NL193282C (ko) |
NO (1) | NO156408C (ko) |
PT (1) | PT75076B (ko) |
SE (1) | SE453595B (ko) |
SU (1) | SU1316556A3 (ko) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6354321A (ja) * | 1985-03-27 | 1988-03-08 | Ajinomoto Co Inc | 血糖降下剤 |
US4783334A (en) * | 1986-01-21 | 1988-11-08 | Chugai Seiyaku Kabushiki Kaisha | Stable solid preparation of thiol ester derivative |
ZA896851B (en) | 1988-09-14 | 1990-06-27 | Hoffmann La Roche | Use of ace-inhibitors |
DE59409631D1 (de) * | 1993-07-15 | 2001-02-15 | Hoffmann La Roche | Pharmazeutische Kombination, die einen Hemmer des Renin-Angiotensin-Systems und einen Endothelin-Antagonisten enthält |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA802420B (en) * | 1979-05-18 | 1981-04-29 | Squibb & Sons Inc | Aminoacyl derivatives of mercaptoacyl amino acids |
-
1981
- 1981-12-29 AT AT0558581A patent/AT377496B/de not_active IP Right Cessation
-
1982
- 1982-05-26 GB GB08215345A patent/GB2102412B/en not_active Expired
- 1982-05-28 CA CA000404054A patent/CA1235120A/en not_active Expired
- 1982-06-02 IL IL65954A patent/IL65954A/xx not_active IP Right Cessation
- 1982-06-16 FI FI822171A patent/FI75804C/fi not_active IP Right Cessation
- 1982-06-16 NO NO821997A patent/NO156408C/no not_active IP Right Cessation
- 1982-06-16 IT IT67772/82A patent/IT1157053B/it active
- 1982-06-16 MX MX193189A patent/MX155724A/es unknown
- 1982-06-16 SU SU823450352A patent/SU1316556A3/ru active
- 1982-06-16 MX MX010799A patent/MX171888B/es unknown
- 1982-06-17 HU HU821976A patent/HU188177B/hu not_active IP Right Cessation
- 1982-06-17 DK DK273082A patent/DK156054C/da not_active IP Right Cessation
- 1982-06-17 CH CH3751/82A patent/CH651825A5/de not_active IP Right Cessation
- 1982-06-18 DE DE19823222779 patent/DE3222779A1/de active Granted
- 1982-06-18 NL NL8202472A patent/NL193282C/nl not_active IP Right Cessation
- 1982-06-18 PT PT75076A patent/PT75076B/pt not_active IP Right Cessation
- 1982-06-18 SE SE8203814A patent/SE453595B/sv not_active IP Right Cessation
- 1982-06-18 ES ES513277A patent/ES513277A0/es active Granted
- 1982-06-19 KR KR8202740A patent/KR890000769B1/ko active
- 1982-06-21 FR FR8210796A patent/FR2508040B1/fr not_active Expired
-
1983
- 1983-03-14 ES ES520582A patent/ES520582A0/es active Granted
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