KR830007630A - 아민유도체의 제조방법 - Google Patents
아민유도체의 제조방법 Download PDFInfo
- Publication number
- KR830007630A KR830007630A KR1019810003735A KR810003735A KR830007630A KR 830007630 A KR830007630 A KR 830007630A KR 1019810003735 A KR1019810003735 A KR 1019810003735A KR 810003735 A KR810003735 A KR 810003735A KR 830007630 A KR830007630 A KR 830007630A
- Authority
- KR
- South Korea
- Prior art keywords
- pyridyl
- dimethylaminomethyl
- formula
- group
- substituted
- Prior art date
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- 150000001412 amines Chemical class 0.000 title claims 4
- 238000000034 method Methods 0.000 title claims 4
- -1 nitroamino Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- FLDCYXOIVORVJI-UHFFFAOYSA-N 2-[[4-[(dimethylamino)methyl]pyridin-2-yl]methylsulfanyl]ethanamine Chemical compound CN(C)CC1=CC=NC(CSCCN)=C1 FLDCYXOIVORVJI-UHFFFAOYSA-N 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- 231100000331 toxic Toxicity 0.000 claims 2
- 230000002588 toxic effect Effects 0.000 claims 2
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 1
- UQGQVSVQNBXMBA-UHFFFAOYSA-N 2-[2-[[4-[(dimethylamino)methyl]pyridin-2-yl]methylsulfanyl]ethylamino]-5-[(5,6-dimethylpyridin-3-yl)methyl]-1h-pyrimidin-6-one Chemical compound CN(C)CC1=CC=NC(CSCCNC=2NC(=O)C(CC=3C=C(C)C(C)=NC=3)=CN=2)=C1 UQGQVSVQNBXMBA-UHFFFAOYSA-N 0.000 claims 1
- GXOLLTTXFMGTHF-UHFFFAOYSA-N 2-[2-[[4-[(dimethylamino)methyl]pyridin-2-yl]methylsulfanyl]ethylamino]-5-[(6-methylpyridin-3-yl)methyl]-1h-pyrimidin-6-one Chemical compound CN(C)CC1=CC=NC(CSCCNC=2NC(=O)C(CC=3C=NC(C)=CC=3)=CN=2)=C1 GXOLLTTXFMGTHF-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 125000004633 N-oxo-pyridyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- IIQFIDKGTDXLBU-UHFFFAOYSA-N benzyl thiohypochlorite Chemical compound ClSCC1=CC=CC=C1 IIQFIDKGTDXLBU-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims 1
- 230000020335 dealkylation Effects 0.000 claims 1
- 238000006900 dealkylation reaction Methods 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical group Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229960003151 mercaptamine Drugs 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- KWBSLRQDOHBJPQ-UHFFFAOYSA-N n-[5-[(6-methylpyridin-3-yl)methyl]-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound C1=NC(C)=CC=C1CC1=CN=C(N[N+]([O-])=O)NC1=O KWBSLRQDOHBJPQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Chemical group 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- 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
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Pyrrole Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (8)
- 다음 일반식(2)의 아민을 다음 일반식(3)의 피리미돈과 반응시키고 존재하는 어떠한 보호기도 제거시키거나 다음 일반식(4)의 구아니딘을 다음 일반식(5)의 화합물과 반응시키고 생성물을 약제학적으로 무독한 산부가염으로 임의 전환시키거나 X가 메틸렌이고 Y가 황인 일반식(1)의 화합물을 제조하기 위하여는 다음 일반식(6)의 화합물을 다음 일반식(7)의 화합물과 반응시키고 존재하는 어떠한 보호기도 제거하며 생성물을 약제학적으로 무독한 산부가염으로 임의 전환시켜서 다음 일반식(1)의 화합물 및 그의 약제학적으로 무독한 산부가염을 제조하는 방법.상기식에서R1및 R2는 C1-C4알킬 또는 이들이 결합된 질소원자와 함께 피롤리디노 또는 피페리디노기를 형성하며Y는 메틸렌 또는 황이며X는 메틸렌 또는 산소(단 Y가 황일때 X는 메틸렌이다)이며Z는 수소 또는 C1-C4알킬이고R5는 수소, C1-C4알킬 또는 -A-B(이때 A는 C1-C4알킬렌이며 B는 하나 또는 그이상의 C1-C4알킬, C1-C4알콕시 또는 하이드록시기로 임의로 치환된 피리딜 또는 N-옥소피리딜기; 퀴놀일, 티아졸일, 푸라닐, 티에닐, 나프틸, 5-(1,3-벤조디옥솔일), 6-(2,3-디하이드로-1,4-벤조디옥시닐); 1 내지 3의 할로겐, C1-C4알콕시, C1-C|4알킬 또는 하이드록시기에 의해 임의로 치환된 페닐기; 5-위치에서 -CH2NR1R2로 치환된 2-푸라닐 또는 2-티에닐기; 3-또는 4-위치에서 -CH2NR1R2로 치환된 페닐기; 5 또는 6- 위치에서 -CH2NR1R2로 치환된 3-피리딜기; 2 위치에서 -CH2NR1R2로 치환된 4-피리딜기; 또는 4 또는 5위치에서 -CH2NR1R2로 치환된 2-피리딜기이다.Q는 니트로아미노, 저급알킬티오, 벤질티오, 염소, 브롬 또는 1급아민으로 치환될 수 있는 기타기이며R은 R5와 동일하거나 -A-B의 보호된 유도체일 수 있으며 일반식(5)에서R5는 저급알킬이며L은 티올로 치환될 수 있는 기이다.
- 상기 제1항에 있어서, 일반식(2)의 아민을 Q가 니트로아미노인 일반식(3)의 피리미돈과 반응시키며 반응은 저급알칸올, 피리딘 또는 아니솔중 환류온도에서 수행되는 제법.
- 상기 제1항 또는 제2항에 있어서, 화합물(3) 또는 (5)중 B가 6-또는 2-저급알콕시 또는 벤질옥시치환체를 가지는 3-또는 4-피리딜기이며 초기 생성물을 에탄올성 염산 또는 브롬화수소산을 사용하여 탈알킬화시켜서 B가 6- 또는 2-하이드록시기를 가지는 3-또는 4-피리딜인 일반식(1)의 화합물을 수득하는 제법.
- 상기 제1항 또는 제2항에 있어서 X가 메틸렌이고 Y가 황이며 R1및 R2가 둘다 메틸이고 R5가 -A-B(A는 메틸렌이다)의 제법.
- 상기 제4항에 있어서, B가 3-피리딜, 6-메틸-3-피리딜, 5,6-디메틸-3-피리딜, 6-메톡시-3-피리딜, 2-메톡시-4-피리딜, 6-하이드록시-3-피리딜, 2-하이드록시-4-피리딜, N-옥소-3-피리딜, N-옥소-6-메틸-3-피리딜, N-옥소-4-피리딜, 3-퀴놀일, 2-티아졸일, 2-푸라닐, 5-디메틸아미노메틸-2-푸라닐, 5-디메틸아미노메틸-2-티에닐, 3-(디메틸아미노메틸)-페닐, 4-(디메틸아미노메틸)페닐, 5-디메틸아미노메틸)-3-피리딜, 6-(디메틸아미노메틸)-3-피리딜, 2-(디메틸아미노메틸)-4-피리딜, 4-(디메틸아미노메틸)-2-피리딜 또는 5-(디메틸아미노메틸)-2-피리딜인 제법.
- 상기 제2항에 있어서 2-(4-디메틸아미노메틸-2-피리딜메틸티오)에틸아민을 2-니트로아미노-5-(6-메틸-3-피리딜메틸)-4-피리미돈과 반응시켜서 2-[2-(4-디메틸아미노메틸-2-피리딜메틸티오)에틸아미노]-5-(6-메틸-3-피리딜메틸)-4-피리미돈을 수득하는 제법.
- 상기 제2항에 있어서, 2-(4-디메틸아미노메틸-2-피리딜메틸티오)에틸아민을 2-니트로아미노-5-(5,6-디메틸-3-피리딜메틸)-4-피리미돈과 반응시켜서 2-[2-(4-디메틸아미노메틸-2-피리딜메틸티오)에틸아미노]-5-(5,6-디메틸-3-피리딜메틸)-4-피리미돈을 수득하는 제법.
- 다음 일반식(6)의 피리딜 유도체를 시스테아민과 반응시켜서 다음 일반식(2)의 아민을 제조하는 방법.상기식에서R1및 R2는 C1-C4알킬이거나 이들이 결합된 질소원자와 함께 피롤리디노 또는 피레리디노기를 형성하며Y는 황이고X는 메틸렌이며L은 티올로 치환될 수 있는 기이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8031685 | 1980-10-01 | ||
| GB8031685 | 1980-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR830007630A true KR830007630A (ko) | 1983-11-04 |
Family
ID=10516418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810003735A KR830007630A (ko) | 1980-10-01 | 1981-09-30 | 아민유도체의 제조방법 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4385058A (ko) |
| EP (1) | EP0049173B1 (ko) |
| JP (1) | JPS5791986A (ko) |
| KR (1) | KR830007630A (ko) |
| AT (1) | ATA420581A (ko) |
| AU (1) | AU547215B2 (ko) |
| CA (1) | CA1170261A (ko) |
| DD (1) | DD200469A5 (ko) |
| DE (1) | DE3171234D1 (ko) |
| DK (1) | DK435681A (ko) |
| ES (1) | ES505898A0 (ko) |
| FI (1) | FI813054L (ko) |
| GR (1) | GR75783B (ko) |
| IL (1) | IL63913A0 (ko) |
| NO (1) | NO813326L (ko) |
| PH (2) | PH17948A (ko) |
| PL (1) | PL233256A1 (ko) |
| PT (1) | PT73691B (ko) |
| RO (1) | RO82214A (ko) |
| YU (1) | YU236881A (ko) |
| ZA (1) | ZA816794B (ko) |
| ZW (1) | ZW21281A1 (ko) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA823149B (en) * | 1981-05-27 | 1983-03-30 | Smithkline Beckman Corp | Chemical process |
| PT74865B (en) * | 1981-05-27 | 1983-12-07 | Smithkline Beckman Corp | Process of preparing a 2-(pyridylbutylamino)-pyrimidone and of its pharmaceutically acceptable salts |
| US4808589A (en) * | 1982-02-20 | 1989-02-28 | Smith Kline & French Laboratories Limited | Pyrimidone derivatives |
| EP0089153B1 (en) * | 1982-03-17 | 1986-09-24 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
| DE3365869D1 (en) * | 1982-07-30 | 1986-10-09 | Smith Kline French Lab | Amino pyrimidinones and their preparation |
| PT77287B (en) * | 1982-10-01 | 1986-02-04 | Smith Kline French Lab | Compound |
| AU1956283A (en) * | 1982-10-02 | 1984-04-05 | Smith Kline & French Laboratories Limited | 1-(3-(4-(substited aminomethyl)pyrid-2-yl-oxy)-prop-1-yl- amino) - 2-aminocyclobut-i-ene-3,4-diones |
| PT77623B (en) * | 1982-11-25 | 1986-03-19 | Smith Kline French Lab | Process for the preparation of a small class of histamine h2-antagonists |
| JO1274B1 (en) * | 1982-12-03 | 1985-04-20 | سيدني ساخ جورج | Pyridine derivatives |
| DE3374313D1 (de) * | 1982-12-23 | 1987-12-10 | Smith Kline French Lab | Aminopyrimidinone derivatives as histamine h1-antagonists |
| PT77856B (en) * | 1982-12-23 | 1986-04-16 | Smith Kline French Lab | Pyridine derivatives |
| GB8311443D0 (en) * | 1983-04-27 | 1983-06-02 | Smith Kline French Lab | Chemical compounds |
| GB8318638D0 (en) * | 1983-07-09 | 1983-08-10 | Smith Kline French Lab | Chemical compounds |
| GB8319874D0 (en) * | 1983-07-23 | 1983-08-24 | Smith Kline French Lab | Compounds |
| GB8320505D0 (en) * | 1983-07-29 | 1983-09-01 | Smith Kline French Lab | Chemical compounds |
| US4772704A (en) * | 1983-09-21 | 1988-09-20 | Bristol-Myers Company | 2,5-disubstituted-4(3H)-pyrimidones having histamine H2 -receptor antagonist activity |
| GB8332091D0 (en) * | 1983-12-01 | 1984-01-11 | Smith Kline French Lab | Chemical compounds |
| GB8421427D0 (en) * | 1984-08-23 | 1984-09-26 | Smith Kline French Lab | Chemical compounds |
| CA1275097A (en) * | 1984-10-02 | 1990-10-09 | Fujio Nohara | Pyridyloxy derivatives |
| GB8601816D0 (en) * | 1986-01-25 | 1986-02-26 | Smith Kline French Lab | Pyridine derivatives |
| US4931452A (en) * | 1987-11-10 | 1990-06-05 | The Dow Chemical Company | N-cyanomethyl-2-pyridinone insecticides |
| JP2807577B2 (ja) * | 1990-06-15 | 1998-10-08 | エーザイ株式会社 | 環状アミド誘導体 |
| WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1419994A (en) * | 1973-05-03 | 1976-01-07 | Smith Kline French Lab | Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them |
| IN146736B (ko) * | 1975-10-02 | 1979-08-25 | Smith Kline French Lab | |
| US4218452A (en) * | 1975-10-02 | 1980-08-19 | Smith Kline & French Laboratories Limited | Substituted 4-pyrimidone compounds, compositions and methods of use |
| US4145546A (en) * | 1975-10-02 | 1979-03-20 | Smith Kline & French Laboratories Limited | 4-Pyrimidone compounds |
| US4154834A (en) * | 1975-12-29 | 1979-05-15 | Smith Kline & French Laboratories Limited | Substituted isocytosines having histamine H2 -antagonist activity |
| MW5076A1 (en) * | 1975-12-29 | 1978-02-08 | Smith Kline French Lab | Pharmacologicalle active compounds |
| IN151188B (ko) * | 1978-02-13 | 1983-03-05 | Smith Kline French Lab | |
| US4227000A (en) * | 1978-04-11 | 1980-10-07 | Smith Kline & French Laboratories Limited | Intermediates in the process for making histamine antagonists |
| IL57416A (en) * | 1978-05-30 | 1983-03-31 | Smith Kline French Lab | Nitro compounds,processes for preparing them and compositions containing them |
| ZA793443B (en) * | 1978-07-26 | 1980-12-31 | Glaxo Group Ltd | Heterocyclic derivatives |
| US4250316A (en) * | 1978-11-24 | 1981-02-10 | Bristol-Myers Company | Pyridyl guanidine anti-ulcer agents |
| US4255428A (en) * | 1979-03-24 | 1981-03-10 | Smith Kline & French Laboratories Limited | 5-(Hydroxypyridylalkyl)-4-pyrimidones |
| CA1140129A (en) * | 1979-08-21 | 1983-01-25 | Ronald J. King | 4-pyrimidone derivatives |
-
1981
- 1981-08-28 ZW ZW212/81A patent/ZW21281A1/xx unknown
- 1981-09-16 US US06/302,941 patent/US4385058A/en not_active Expired - Fee Related
- 1981-09-17 PT PT73691A patent/PT73691B/pt unknown
- 1981-09-22 IL IL63913A patent/IL63913A0/xx unknown
- 1981-09-26 RO RO81105409A patent/RO82214A/ro unknown
- 1981-09-30 CA CA000386988A patent/CA1170261A/en not_active Expired
- 1981-09-30 KR KR1019810003735A patent/KR830007630A/ko unknown
- 1981-09-30 PH PH26291A patent/PH17948A/en unknown
- 1981-09-30 JP JP56156896A patent/JPS5791986A/ja active Granted
- 1981-09-30 ES ES505898A patent/ES505898A0/es active Granted
- 1981-09-30 GR GR66162A patent/GR75783B/el unknown
- 1981-09-30 PL PL23325681A patent/PL233256A1/xx unknown
- 1981-09-30 PH PH26291A patent/PH17950A/en unknown
- 1981-09-30 NO NO813326A patent/NO813326L/no unknown
- 1981-10-01 AU AU75951/81A patent/AU547215B2/en not_active Ceased
- 1981-10-01 DK DK435681A patent/DK435681A/da not_active Application Discontinuation
- 1981-10-01 AT AT0420581A patent/ATA420581A/de not_active Application Discontinuation
- 1981-10-01 YU YU02368/81A patent/YU236881A/xx unknown
- 1981-10-01 FI FI810354A patent/FI813054L/fi not_active Application Discontinuation
- 1981-10-01 ZA ZA816794A patent/ZA816794B/xx unknown
- 1981-10-01 EP EP81304540A patent/EP0049173B1/en not_active Expired
- 1981-10-01 DD DD81233796A patent/DD200469A5/de unknown
- 1981-10-01 DE DE8181304540T patent/DE3171234D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| YU236881A (en) | 1984-02-29 |
| IL63913A0 (en) | 1981-12-31 |
| EP0049173A3 (en) | 1982-06-30 |
| JPS5791986A (en) | 1982-06-08 |
| PL233256A1 (ko) | 1982-11-08 |
| EP0049173A2 (en) | 1982-04-07 |
| EP0049173B1 (en) | 1985-07-03 |
| RO82214B (ro) | 1983-06-30 |
| NO813326L (no) | 1982-04-02 |
| PT73691B (en) | 1982-12-10 |
| DK435681A (da) | 1982-04-02 |
| AU7595181A (en) | 1982-04-08 |
| FI813054L (fi) | 1982-04-02 |
| DE3171234D1 (en) | 1985-08-08 |
| DD200469A5 (de) | 1983-05-04 |
| PH17950A (en) | 1985-02-11 |
| PT73691A (en) | 1981-10-01 |
| ATA420581A (de) | 1985-03-15 |
| ES8301966A1 (es) | 1983-01-01 |
| PH17948A (en) | 1985-02-11 |
| JPS6328069B2 (ko) | 1988-06-07 |
| US4385058A (en) | 1983-05-24 |
| ZA816794B (en) | 1982-10-27 |
| ZW21281A1 (en) | 1981-11-18 |
| GR75783B (ko) | 1984-08-02 |
| ES505898A0 (es) | 1983-01-01 |
| CA1170261A (en) | 1984-07-03 |
| RO82214A (ro) | 1983-07-07 |
| AU547215B2 (en) | 1985-10-10 |
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