KR840004745A - 궤양 치료제인 2-구아니디노-4-(2-치환된-아미노-4-이미다졸릴)-티아졸의 제조방법 - Google Patents
궤양 치료제인 2-구아니디노-4-(2-치환된-아미노-4-이미다졸릴)-티아졸의 제조방법 Download PDFInfo
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- KR840004745A KR840004745A KR1019830001962A KR830001962A KR840004745A KR 840004745 A KR840004745 A KR 840004745A KR 1019830001962 A KR1019830001962 A KR 1019830001962A KR 830001962 A KR830001962 A KR 830001962A KR 840004745 A KR840004745 A KR 840004745A
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- Prior art keywords
- alkyl
- formula
- bromo
- compound
- disubstituted
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- 238000000034 method Methods 0.000 title claims 6
- -1 2-guanidino-4- (2-substituted-amino-4-imidazolyl) -thiazole Chemical class 0.000 title 1
- 208000025865 Ulcer Diseases 0.000 title 1
- 231100000397 ulcer Toxicity 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- QIULLFCKBYDMCJ-UHFFFAOYSA-N 1-(5-bromo-1H-imidazol-2-yl)ethanone Chemical compound CC(=O)C1=NC=C(Br)N1 QIULLFCKBYDMCJ-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000003125 aqueous solvent Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- TUFOJIVMBHBZRQ-UHFFFAOYSA-N 1-(1h-imidazol-5-yl)ethanone Chemical compound CC(=O)C1=CN=CN1 TUFOJIVMBHBZRQ-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- QYMDEOQLJUUNOF-UHFFFAOYSA-N Pinoline Natural products C1NCCC2=C1NC1=CC=C(OC)C=C12 QYMDEOQLJUUNOF-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- MZJUGRUTVANEDW-UHFFFAOYSA-N bromine fluoride Chemical compound BrF MZJUGRUTVANEDW-UHFFFAOYSA-N 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
- Analysing Materials By The Use Of Radiation (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Lubricants (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (7)
- (a) 일반식(Ⅳ)의 옥사졸을 수성 용매중에서 일반식 H2NR5또는 HNR2R3(여기서 R2,R3및 R5는후술하는 바와 같다)의 아민 과량과 반응시켜 일반식(Ⅴ)의 5-아세틸 이미다졸을 형성하며; (b) 일반식 (Ⅴ)의 이미다졸을 산조건하에 브롬화하여 일반식(Ⅵ)의 브로모 아세틸 이미다졸을 형성하고; (c) 일반식(Ⅵ)의 브로모 아세틸이미다졸을 구조식의 화합물과 커플링시켜 일반식(Ⅲ) 화합물을 생성시킴을 특징으로 하는 일반식(Ⅲ) 화합물의 제조방법.상기 식에서,R4는 NHR5또는 NR2R3이며, R5은 (C1내지 C12) 알킬, (C3내지 C9)사이클로, (C6내지 C11)-피리딜알킬이거나 클로로, 브로모, 플루오로 (C1내지 C3) 알킬, (C1내지 C3) 알콕시 또는트리플루오로 메틸로페닐그룹상에서 임의로 단일 또는 이치환된(C7내지 C12)페닐 알킬이며; R2및 R3는각각 독립적으로 (C1내지 C12) 알킬 또는 클로로, 브로모, 플루오르, (C1내지 C3) 알킬, (C1내지 C8)알콕시 또는 트리플루오로메틸로 페닐그룹상에 임의로 단일 또는 이치환된((C7내지 C12)페닐 알킬이거나,R1및 R3는 이들이 부착된 질소와 함께 피롤리딘, 피페리딘 또는 모르폴린환을 형성한다.
- 제1항에 있어서, R4가 NHR5이고 R5가 (C1내지 C9) 알킬인 방법.
- 제2항에 있어서, R5가 n-헥실인 방법.
- 제1항에 있어서, 일반식(Ⅰ) 화합물을 결정성 하이드로브로마아드 염으로써 분리함을 특징으로 하는 방법.
- 일반식(Ⅳ)의 옥사졸을 수성 용매중에서 일반식 H2NR5또는 HNR2R3(여기서 R2,R3및 R5는|후술하는 바와 같다)의 아민 과량과 반응시킴을 특징으로하여 일반식(Ⅴ)의 화합물을 제조하는 방법.상기 식에서, R4는 NHR5또는 NR2R3이며, R5는 (C1내지 C12)알킬, (C3내지 C8)사이클로알킬, (C6내지C11)피리딜알킬이거나 클로로, 브로모, 플루오로,(C1내지 C3)알킬, (C1내지 C3)알콕시 또는 트리플루오로메틸로 페닐그룹상에 임의로 단일 또는 이치환된된(C7내지 C12)페닐 알킬이며;R2및 R3는 각각 독립적으로, (C1내지 C12)알킬,또는 클로로, 브로모, 플로오로, (C1내지 C3)알킬, (C1내지 C3)알콕시 또는 트리플루오로메틸로 페닐그룹상에 단일 또는 이치환된된(C7내지 C12)페닐알킬이거나, R2및 R3는 이들이 부착된 질소와 함께 피롤리딘, 피페리딘, 퍼하이드로-1H-아제핀 또는 모르폴린환을 형성한다.
- 제5항에 있어서 R4가 NHR5이고 R5가 (C1내지 C12)알킬인 방법,
- 제 6항에 있어서 R5가 n-헥실인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/376,486 US4435396A (en) | 1982-05-10 | 1982-05-10 | Antiulcer 2-guanidino-4-(2-substituted-amino-4-imidazolyl)thiazoles and process therefor |
| US376,486 | 1982-05-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840004745A true KR840004745A (ko) | 1984-10-24 |
| KR860000931B1 KR860000931B1 (ko) | 1986-07-19 |
Family
ID=23485203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830001962A KR860000931B1 (ko) | 1982-05-10 | 1983-05-09 | 궤양 치료제인 2-구아니디노-4-(2-치환된-아미노-4-이미다졸릴)-티아졸의 제조방법 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4435396A (ko) |
| EP (1) | EP0094191B1 (ko) |
| JP (1) | JPS58206588A (ko) |
| KR (1) | KR860000931B1 (ko) |
| AT (1) | ATE33649T1 (ko) |
| AU (2) | AU539244B2 (ko) |
| CA (1) | CA1201120A (ko) |
| CS (1) | CS252461B2 (ko) |
| DD (1) | DD209828A5 (ko) |
| DE (1) | DE3376322D1 (ko) |
| DK (1) | DK163829B (ko) |
| EG (1) | EG17029A (ko) |
| ES (1) | ES522223A0 (ko) |
| FI (1) | FI78481C (ko) |
| GR (1) | GR79279B (ko) |
| GT (1) | GT198302123A (ko) |
| HU (2) | HU190899B (ko) |
| IE (1) | IE55229B1 (ko) |
| IL (1) | IL68630A (ko) |
| NO (1) | NO159932C (ko) |
| NZ (1) | NZ204158A (ko) |
| PL (1) | PL141199B1 (ko) |
| PT (1) | PT76662B (ko) |
| SU (1) | SU1195907A3 (ko) |
| YU (1) | YU42857B (ko) |
| ZA (1) | ZA833286B (ko) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4673677A (en) * | 1983-10-03 | 1987-06-16 | Pfizer Inc. | Method for treatment of gastrointestinal disorders |
| US4554276A (en) * | 1983-10-03 | 1985-11-19 | Pfizer Inc. | 2-Amino-5-hydroxy-4-methylpyrimidine derivatives |
| US4560690A (en) * | 1984-04-30 | 1985-12-24 | Pfizer Inc. | 2-(N-substituted guanidino)-4-hetero-arylthiazole antiulcer agents |
| US4632993A (en) * | 1984-10-11 | 1986-12-30 | Pfizer Inc. | Process for making 2-guanidino-4-(2-methyl-4-imidazolyl) thiazole dihydrobromide |
| US4636498A (en) * | 1984-10-11 | 1987-01-13 | Pfizer Inc. | Formulation of antiinflammatory drugs |
| WO1986003203A1 (en) * | 1984-11-22 | 1986-06-05 | Yoshitomi Pharmaceutical Industries, Ltd. | Thienylthiazole derivatives |
| US4814341A (en) * | 1986-08-26 | 1989-03-21 | Reiter Lawrence A | 2-guanidino-4-(2-furyl) thiazoles as antiulcer agents |
| ATE66477T1 (de) * | 1986-08-29 | 1991-09-15 | Pfizer | 2-guanidino-4-aryl-thiazole fuer die behandlung von peptischen geschwueren. |
| ATE106884T1 (de) * | 1986-10-29 | 1994-06-15 | Pfizer | Verfahren zur herstellung von 2-(1-pentyl-3- guanidino)-4-(2-methyl-4-imidazolyl)thiazol und dessen kristallinisches dihydrochlorid-trihydrat. |
| AU6436394A (en) * | 1993-06-15 | 1995-01-03 | Pfizer Inc. | H2-antagonists as immune stimulants in bacterial infections of cattle or swine |
| KR101406433B1 (ko) | 2008-09-22 | 2014-06-13 | 카이맨 케미칼 컴파니 인코포레이티드 | Ｈ-ｐｇｄｓ 억제제로서 다중헤테로아릴 화합물 및 프로스타글란딘 ｄ2 매개된 질병의 치료를 위한 그의 용도 |
| EP4196793A1 (en) | 2020-08-11 | 2023-06-21 | Université de Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3519637A (en) | 1966-12-06 | 1970-07-07 | Hoffmann La Roche | 1-(4-thiazolylmethyl)nitroimidazole derivatives |
| DE2142585A1 (de) * | 1971-08-20 | 1973-02-22 | Schering Ag | 2-(5-nitro-2-thiazolyl)-benzimidazole |
| FR2284601A1 (fr) * | 1974-09-10 | 1976-04-09 | Inst Francais Du Petrole | Composes guanidino-heterocycliques alkyles, leur preparation et leur utilisation comme additifs pour carburants et lubrifiants |
| US4220654A (en) | 1979-06-04 | 1980-09-02 | Merck & Co., Inc. | Cyclic imidazole cyanoguanidines |
| US4374843A (en) | 1980-10-14 | 1983-02-22 | Pfizer Inc. | 2-Guanidino-4-heteroarylthiazoles |
-
1982
- 1982-05-10 US US06/376,486 patent/US4435396A/en not_active Expired - Fee Related
-
1983
- 1983-05-03 SU SU833585699A patent/SU1195907A3/ru active
- 1983-05-04 GR GR71297A patent/GR79279B/el unknown
- 1983-05-04 AT AT83302495T patent/ATE33649T1/de not_active IP Right Cessation
- 1983-05-04 DE DE8383302495T patent/DE3376322D1/de not_active Expired
- 1983-05-04 EP EP83302495A patent/EP0094191B1/en not_active Expired
- 1983-05-05 YU YU996/83A patent/YU42857B/xx unknown
- 1983-05-05 CS CS833184A patent/CS252461B2/cs unknown
- 1983-05-06 GT GT198302123A patent/GT198302123A/es unknown
- 1983-05-06 HU HU831581A patent/HU190899B/hu not_active IP Right Cessation
- 1983-05-06 NZ NZ204158A patent/NZ204158A/en unknown
- 1983-05-06 PL PL1983241840A patent/PL141199B1/pl unknown
- 1983-05-06 CA CA000427596A patent/CA1201120A/en not_active Expired
- 1983-05-06 HU HU862387A patent/HU196377B/hu not_active IP Right Cessation
- 1983-05-07 EG EG275/83A patent/EG17029A/xx active
- 1983-05-09 NO NO831632A patent/NO159932C/no unknown
- 1983-05-09 ES ES522223A patent/ES522223A0/es active Granted
- 1983-05-09 DD DD83250744A patent/DD209828A5/de not_active IP Right Cessation
- 1983-05-09 DK DK205883A patent/DK163829B/da not_active Application Discontinuation
- 1983-05-09 ZA ZA833286A patent/ZA833286B/xx unknown
- 1983-05-09 FI FI831595A patent/FI78481C/fi not_active IP Right Cessation
- 1983-05-09 IL IL68630A patent/IL68630A/xx unknown
- 1983-05-09 KR KR1019830001962A patent/KR860000931B1/ko not_active IP Right Cessation
- 1983-05-09 IE IE1061/83A patent/IE55229B1/en unknown
- 1983-05-09 PT PT76662A patent/PT76662B/pt unknown
- 1983-05-09 AU AU14363/83A patent/AU539244B2/en not_active Ceased
- 1983-05-10 JP JP58081601A patent/JPS58206588A/ja active Pending
-
1984
- 1984-07-18 AU AU30815/84A patent/AU566755B2/en not_active Ceased
Also Published As
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| Publication | Publication Date | Title |
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