KR830007628A - 2,4-디아미노-5(치환된)피리미딘의 제조방법 및 이것의 제약학적 조성물 - Google Patents
2,4-디아미노-5(치환된)피리미딘의 제조방법 및 이것의 제약학적 조성물 Download PDFInfo
- Publication number
- KR830007628A KR830007628A KR1019810004348A KR810004348A KR830007628A KR 830007628 A KR830007628 A KR 830007628A KR 1019810004348 A KR1019810004348 A KR 1019810004348A KR 810004348 A KR810004348 A KR 810004348A KR 830007628 A KR830007628 A KR 830007628A
- Authority
- KR
- South Korea
- Prior art keywords
- diamino
- pyrimidine
- amino
- group
- hydrogen
- Prior art date
Links
- -1 2,4-diamino-5 (substituted) pyrimidine Chemical class 0.000 title claims 16
- 238000000034 method Methods 0.000 title claims 9
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 8
- 125000004414 alkyl thio group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 150000001204 N-oxides Chemical class 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical class 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- CSOGBPZNPVMDLW-UHFFFAOYSA-N 5-[(4-methoxynaphthalen-1-yl)methyl]pyrimidine-2,4-diamine Chemical compound C12=CC=CC=C2C(OC)=CC=C1CC1=CN=C(N)N=C1N CSOGBPZNPVMDLW-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 238000004517 catalytic hydrocracking Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- PWAHCQHSJOCQHQ-UHFFFAOYSA-N 4-[(2,4-diaminopyrimidin-5-yl)methyl]-2-methoxynaphthalen-1-ol Chemical compound C=12C=CC=CC2=C(O)C(OC)=CC=1CC1=CN=C(N)N=C1N PWAHCQHSJOCQHQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- GKQJABQIIZIFFZ-UHFFFAOYSA-N 5-[(4-amino-3-methoxynaphthalen-1-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=CC2=C(N)C(OC)=CC=1CC1=CN=C(N)N=C1N GKQJABQIIZIFFZ-UHFFFAOYSA-N 0.000 claims 1
- SAUMGAFMQSWBPZ-UHFFFAOYSA-N 5-[(5-amino-6-methoxyquinolin-8-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12N=CC=CC2=C(N)C(OC)=CC=1CC1=CN=C(N)N=C1N SAUMGAFMQSWBPZ-UHFFFAOYSA-N 0.000 claims 1
- RQRUVIVMJKJWIG-UHFFFAOYSA-N 5-[(5-amino-6-methylquinolin-8-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12N=CC=CC2=C(N)C(C)=CC=1CC1=CN=C(N)N=C1N RQRUVIVMJKJWIG-UHFFFAOYSA-N 0.000 claims 1
- ZYPSBPRHNICRMO-UHFFFAOYSA-N 5-[(7,8-dimethoxy-4h-chromen-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12CC=COC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N ZYPSBPRHNICRMO-UHFFFAOYSA-N 0.000 claims 1
- UEZUWFLRLFLRDB-UHFFFAOYSA-N 5-[(7,8-dimethoxyquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N UEZUWFLRLFLRDB-UHFFFAOYSA-N 0.000 claims 1
- VGRYERWGOVRICR-UHFFFAOYSA-N 5-[(7-methoxy-8-methylsulfanylquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=C(SC)C(OC)=CC=1CC1=CN=C(N)N=C1N VGRYERWGOVRICR-UHFFFAOYSA-N 0.000 claims 1
- JJARGKURGQMCFR-UHFFFAOYSA-N 5-[(7-methoxyquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=CC(OC)=CC=1CC1=CN=C(N)N=C1N JJARGKURGQMCFR-UHFFFAOYSA-N 0.000 claims 1
- HXNJACHLLBRCGW-UHFFFAOYSA-N 5-[(7-methyl-8-pyrrol-1-ylquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=C(N2C=CC=C2)C(C)=CC=1CC1=CN=C(N)N=C1N HXNJACHLLBRCGW-UHFFFAOYSA-N 0.000 claims 1
- DDYFWXNCUMRKPM-UHFFFAOYSA-N 5-[(7-methylquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=CC(C)=CC=1CC1=CN=C(N)N=C1N DDYFWXNCUMRKPM-UHFFFAOYSA-N 0.000 claims 1
- WGGSOKXLUIKILB-UHFFFAOYSA-N 5-[(8-amino-7-chloroquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CC1=CC(Cl)=C(N)C2=NC=CC=C12 WGGSOKXLUIKILB-UHFFFAOYSA-N 0.000 claims 1
- LNNXDSFSUVHODF-UHFFFAOYSA-N 5-[(8-amino-7-ethoxyquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=C(N)C(OCC)=CC=1CC1=CN=C(N)N=C1N LNNXDSFSUVHODF-UHFFFAOYSA-N 0.000 claims 1
- KUMZSUMUTADUQP-UHFFFAOYSA-N 5-[(8-amino-7-methoxyisoquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CN=CC2=C(N)C(OC)=CC=1CC1=CN=C(N)N=C1N KUMZSUMUTADUQP-UHFFFAOYSA-N 0.000 claims 1
- GVNXJSKJOJYPOC-UHFFFAOYSA-N 5-[(8-amino-7-methoxyquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=C(N)C(OC)=CC=1CC1=CN=C(N)N=C1N GVNXJSKJOJYPOC-UHFFFAOYSA-N 0.000 claims 1
- HASOQHQJVLCIDS-UHFFFAOYSA-N 5-[(8-amino-7-methylquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=C(N)C(C)=CC=1CC1=CN=C(N)N=C1N HASOQHQJVLCIDS-UHFFFAOYSA-N 0.000 claims 1
- GEZCGCFDXURYSM-UHFFFAOYSA-N 5-[(8-amino-7-methylsulfanylquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=C(N)C(SC)=CC=1CC1=CN=C(N)N=C1N GEZCGCFDXURYSM-UHFFFAOYSA-N 0.000 claims 1
- MIKKDMSLZZDBIM-UHFFFAOYSA-N 5-[(8-methoxy-7-propylquinolin-2-yl)methyl]pyrimidine-2,4-diamine Chemical compound N=1C2=C(OC)C(CCC)=CC=C2C=CC=1CC1=CN=C(N)N=C1N MIKKDMSLZZDBIM-UHFFFAOYSA-N 0.000 claims 1
- YVZOIUMKCXEFKF-UHFFFAOYSA-N 5-[(8-methoxyquinolin-5-yl)methyl]pyrimidine-2,4-diamine Chemical compound C12=CC=CN=C2C(OC)=CC=C1CC1=CN=C(N)N=C1N YVZOIUMKCXEFKF-UHFFFAOYSA-N 0.000 claims 1
- ZYWHJUCYNRZOBC-UHFFFAOYSA-N 5-[[8-(dimethylamino)-7-methoxyquinolin-5-yl]methyl]pyrimidine-2,4-diamine Chemical compound C=12C=CC=NC2=C(N(C)C)C(OC)=CC=1CC1=CN=C(N)N=C1N ZYWHJUCYNRZOBC-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 238000004380 ashing Methods 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- AIOWJIMWVFWROP-UHFFFAOYSA-N baquiloprim Chemical compound C12=CC=CN=C2C(N(C)C)=C(C)C=C1CC1=CN=C(N)N=C1N AIOWJIMWVFWROP-UHFFFAOYSA-N 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 238000007068 beta-elimination reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002357 guanidines Chemical class 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- 230000008676 import Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000005905 mesyloxy group Chemical group 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/64—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with oxygen atoms directly attached in position 8
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- (가) (i) 하기 구조식 화합물(Ⅸ) 혹은 (X)의 화합물과 구아니딘염을 반응시킴:(ii) 하기 구조식 화합물(XI)과 C1-4알카놀에서 수산화나트륨 혹은 칼륨과 반응시키고, 구아니연을 첨가함;(iii) 하기 구조식 화합물(XⅡ)와 암모니아와 같은 아민화제와 반응시키고 이후 R27이 할로겐원자일때 수소화분해로 이것을 제거함:(iv) 하기 구조식 화합물(XⅢ)과 하기 구조식 화합물(XIV)을 반응시키고 T가 C1-4알킬티오일때 수소화분해로 수소로 전이하거나 흑은 T가 수신기일때 이것을 매실래이트 혹은 토실래이트 유도체 혹은 티오, 알킬티오 혹은 할로겐으로 전화하며 이것을 수소화분해로 제거함:(다) 페닐환의 4-위치가 히드록시, 아미노 혹은 치환된 아미노로 치환된 구조식(I)의 화합물을 제조할 필요가 있을때 구조식(XVII)화합물과 2,4-디아미노-5-히드록시메틸피리미딘과 반응시킴:이후 임의로 생성된 구조식(I)의 한가지 화합물을 상술한 여러변의 법에 따라 변이할 수 있는 하기 구조식(I)의 화합물 혹은 염, N-산화물 혹은 이것의 아실유도체를 제조하는 방법:윗식에서는 임의로 이 원자를 지니는 육원자환으로 두 페닐환과는 임의로 치환되는데 단가 이 원자를 지니지 아니할때 두 페닐 혹은가 단독으로 페닐환의 4-위치에서 수산기로 치환되어야 하며; 페닐환의 6-위치에 근접한의 원자에 복착한 치환물이 없는 경우는 제외함.R23은 C1-4알킬기임.R24는 C1-4알콕시기 혹은 아미노, C1-4알킬아미노, 벤질아미노, 디(C1-4)알킬아미노, 나프탈아미노, 임의 치환된 아닐로, 모포리노, 피페리디노 혹은 N-메틸피페라지노기이며 아닐로기가 가장 우선하는 것으로서 친핵성 분리기이고,R25는 알콕시카르보닐 혹은 알데히드기임.R26은 C1-4알킬티오기 혹은 할로겐원자와 같은 아미노기 혹은 분리기임.R27은 수소 혹은 할로겐원자로서, 단 두 R26기는 아미노기가 될 수 없음.Z는 할로겐원자임T는 히드록시 혹은 C1-4알킬티오기임.
- 청구범위 1공정에 있어서, 다음 구조식(Ⅱ)의 화합물 또는 이들의 염, N-산화물 또는 아실유도체를 제조하는방법.상기 구조식에서는 X가 N= 또는 CH=인 경우 3중결합을 포함하는 6원자환, X가 페닐환의 -0-인접 내지 5-위치인 경우 2중결합, -N=, -CH=, -CH2- 또는 NR5- X가 페닐환의 -0-인접 내지 5-위치인 경우에서 하나의 이중결합, -CH2- 또는 NR2- 상기에서 R5는 수소, C1-4알킬 또는 그룹 -COR6상기에서 R6은 수소, C1-4알킬, C1-4알콕시 또는 아미노, R1과 R2는 같거나 또는 다르고 각기 수소, 할로겐, C1-4알킬, C1-4알킬티오 또는 할로겐, 히드록시에 의해 임의로 치환된 C1-4알콕시 또는 C1-2알콕시 또는 R1과 R2는 그룹 C=O, C=S 또는를 위한 같은 탄소원자에 연결된다. R3와 R4는 같거나 또는 다르고 각기 수소, 할로겐, C2-4알켄일, C2-4알켄일옥시, 니트로, 시아노, 히드록시, 머캡토, 그룹 -OSO2R7또는 -S(0)n상기에서 R7은 C1-3알킬이고 n은 0,1 또는 2, 그룹 -COR8상기에서 R8은 메틸, 에틸, 메톡시, 에톡시, 아미노, 메틸아미노, 에틸아미노, 디메틸아미노 또는 디에틸아미노 또는 각기 하나 또는 다수 C1-4알킬에 의해 임의로 치환된 아미노 또는 아실 또는 5 또는 6원자헤테로사이클릭환의 질소원자 형성부분, C1-4알킬 또는 할로겐, 히드록시에 의해 임의로 치환된 C1-4알콕시 또는 C1-2알콕시, 또는 R3와 R4는 함께 메틸렌디옥시그룹을 형성; R1,R2와 R3가 함께 수소일때 X가 CH=, 수소 또한 R4가 히드록시가 아닌 것을 제외하고 R1와 R2는 페닐환의 6-위치에 인접한 탄소원자상 치환체가 아니고 X가 -0-일때 할로겐원자 또는 X에 인접한 탄소원자상 알콕시그룹이 아니다.
- 청구범위 1에 있어서, 구조식(Ⅲ)의 화합물 또는 이들의 염, 산화물 또는 아싱유도체를 제조하는 방법.상기 구조식에서(X), R1과 R2는 상기에서 언급한 것이고 R9과 R10은 같거나 또는 다른 것이고, 각기 수소, 할로겐,C2-4알켄일, C2-4알켄일옥시, 니트로, 그룹 NR11R12상기에서 R11과 R12는 같거나 또는 다른 것이고 각기 수메틸 또는 에텔 또는 5 또는 6원자헤테로시클릭환을 형성하는 NR11R12시아노, 하이드록시, 그룹-S(O)nR7또는 전에 언급한 바와 같은 COR8또는 C1-4알킬 또는할로겐, 하이드록시에 의해 임으로 치환된 C1-4알콕시 또는 C1-3알콕시;R9과 R10은 둘다 수소 또는 할로겐이 아닌 것을 제외하며; R1과 R2는 페닐환의 6-위치에 인접한 탄소원자상 치환체가 아니고 X가 -0-일때 X에 인접한 탄소원자상 할로겐 또는 알콕시 치환체가 아니다.
- 청구범위 1에 있어서, 구조식(V)의 화합물 또는 이들의 염, N- 산화물 또는이들의 유도체를 제조하는 방법.상기에서R9과 R10은 R9과 R10이 둘다 수소 또는 할로겐이 아니고 R15은 수소원자 또는 C1-3알킬그룹인 것을 제외한 것인 전에 언급한 것이다.
- 청구범위 1에 있어서, 구조식(Ⅵ)의 화합물 또는 염, N-산화물 또는 이들의 아실유도체를 제조하는 방법.상기 구조식에서(N)은 질소원자를 포함하는 6원자헤테로시클릭환이고 R2,R9과 R10은 전에 언급한 것이고 R16은 수소, 할로겐, C1-3알킬티오, 할로겐, 히드록시에 의해 임의로 치환된 C1-3알콕시 또는 R9과 R10이 둘다 수소또는 할로민이 아닌 것을 제외한C1-2알콕이고 R2및 R16은 페닐환의 6위치에 인접한 탄소원자상 치환체가 아니다.
- 청구범위 1에 있어서, 구조식(Ⅶ)의 화합물 또는 염, N-산화물 또는 이들의 아실유도체를 제조하는 방법.상기 구조식에서R2,R9,R10과 R16은 R2,R9과 R16이 모두 수소이고 R10이 수소 또는 히드록시가 아닌 것을 제외한 상기 언급한 것이다.
- 청구범위 1에 있어서, 구조식(Ⅷ)의 화합물 또는 염 또는 이들의 아실유도체를 제조하는 방법.상기 구조식에서R17과 R18은 함께 메틸렌-디옥시그룹을 형성하거나 또는 R17은 수소, 할로겐, C1-4알킬, C1-4알콕시 C2-4알켄일, 아미노, 치환된 아미노, 트리플루오로메틸, 그룹 -COR21상기에서 R21은 C1-4알킬 또는 C1-4알콕시, 또는 그룹 -OSO2R22상기에서 R22는 C1-4알킬; R18은 할로겐, C1-4알칼, C2-4알켄일, 히드록시, 아미노, 모노- 또는 디- C1-4알킬치환된 아미노, 머캡토, C1-4알킬티오, 트리플루오로메틸, 그룹, -COR21또는 그룹 -OSO2R22상기에서 R21과 R22은 전에 언급한 것이고 R19은 수소 =0, =S,(CH3)2할로겐, C1-4알킬; R20은 수소 또는 메틸, X는 산소, 질소 또는 -NH- 또는 -CH=그룹이고 점선은 X가 산소원자일때 점선이 이중결합을 나타내지 않는 것에 인접한 것을 제외한 단일 또는 이중결합을 나타내고 X가 -CH=이고 R17,R19과 R20이 모두 수소일때, R18은 히드록시와 수소가 아니다.
- i) 구조식(XV)의 화합물로부터 그룹 Y의 β-제거와 ii) 구조식(XVI)의 화합물의 환화에 의해 다음 구조식(XIV)의 화합물을 제조하는 방법.상기 구조식에서R1내지 R4는 전에 언급한 것이고,Y는 히드록시, 치환된 설포닐옥시, 예를들면 메질옥시 또는 토질옥시, 알킬티오, 페닐티오 또는 할로겐같은 분리이고,두 그룹 R28은 같거나 또는 다르고 각기 수소 또는 C1-4알킬티오이다.
- 청구범위 1내지 7에 있어서,다음 그룹으로부터 선택된 화합물 또는 염 또는 이들의 N-산화물을 제조하는 방법.2,4-디아미노-5-(7,8-디메톡시-2H-1-벤조피린-5-일메틸)피리미딘.2,4-디아미노-5-(3,4-디하이드로-7,8-디메톡시-2H-1-벤조피린-5-일메틸)피리미딘.2,4-디아미노-5-(8-메톡시-5-퀴놀일메틸)피리미딘,2,4-디아미노-5-(4-메톡시-1-나프틸메틸)피리미딘,2,4-디아미노-5-(4-메톡시-1-나프틸메틸)피리미딘,2,4-디아미노-5-(7,8-디메톡시-2-메틸-2H-1-벤조피린-5-일메틸)피리미딘.2,4-디아미노-5-(7,8-디메톡시-2,2-디메틸-2H-1-벤조피린-5-일메틸)피리미딘.2,4-디아미노-5-(8-아미노-7-메틸-5-퀴놀일메틸)피리미딘,2,4-디아미노-5-(7,8-디메톡시-2-옥소-2H-1-벤조피린-5-일메틸)피리미딘.2,4-디아미노-5-(7,8-디메톡시-2-메틸-4H-1-벤조피린-5-일메틸)피리미딘.5-(7-알릴-8-히드록시-2-메틸-5퀴놀일메틸)-2,4-디아미노피리미딘,5-(7-알릴-8-히드록시-5-퀴놀일메틸-2,4-디아미노피리미딘,5-(7-알릴-8-메톡시-5-퀴놀일메틸)-2,4-디아미노피리미딘,5-(7-알릴-8-메록시-2-메틸-2-메틸-5-퀴놀일메틸)-2,4-디아미노피리미딘,2,4-디아미노-5-(8-아미노-7-메톡시-5-퀴놀일메틸)피리미딘,2,4-디아미노-5-(8-디메틸아미노-7-메톡시-5-퀴놀일메틸)피리미딘,2,4-디아미노-5-(8-(1-피롤릴)-7-메틸-5-퀴놀일메틸)피리미딘,2,4-디아미노-5-(8-디메틸아미노-7-메틸-5-퀴놀일메틸)피리미딘,2,4-디아미노-5-(8-메톡시-7-프로필퀴놀일메틸)피리미딘,2,4-디아미노-5-(7,8-디메톡시-5-퀴놀일메틸)피리미딘,2,4-디아미노-5-(7-메틸-5-퀴놀일메틸)피리미딘,4-아미노-5-(7,8-디메톡시-2H-1-벤조피란-5-일메틸-2-글리신아미도피리미딘,2,4-디아미노-5-(8-아미노-7-에톡시-5-퀴놀일메틸)피리미딘,2,4-디아미노-5-(8-아미노-7-메틸티오-5-퀴놀일메틸)피리미딘,2,4-디아미노-5-(8-아미노-7-클로로-5-퀴놀일메틸)피리미딘,2,4-디아미노-5-(7-메톡시-5-퀴놀일메틸)피리미딘,2,4-디아미노-5-(7-메톡시-8-메틸티오-5-퀴놀일메틸)피리미딘,5-(7-알릴-8-(2-메톡시에톡시)-5-퀴놀일메틸)-2,4-디아미노피리미딘,2,4-디아미노-5-(5-아미노-6-메틸-8-퀴놀일메틸)피리미딘,2,4-디아미노-5-(5-아미노-6-메톡시-8-퀴놀일메틸)피리미딘,2,4-디아미노-5-(8-아미노-7-메톡시-5-이소퀴놀일메틸)피리미딘,5-(7-알릴-8-(2-메톡시-5-(1,2,3,4-테트라히드로퀴놀일)메틸-2,4-디아미노피리미딘,2,4-디아미노-5-(4-아미노-3-메톡시-1-나프틸메틸)피리미딘,2,4-디아미노-7-(7-메톡시-8-니트로-5-퀴놀일메틸)피리미딘,2,4-디아미노-5-(7,8-디메톡시-4H-1-벤조피란-5-일메틸)피리미딘,2,4-디아미노-5-(4-히드록시-3-메톡시-1-나프틸메틸)피리미딘,2,4-디아미노-5-(3,4-디메톡시-1-메톡시-1-나프틸메틸)피리미딘,2,4-디아미노-5-(4-아미노-3,6-메톡시-1-나프틸메틸)피리미딘,※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8036135 | 1980-11-11 | ||
| GB36135 | 1980-11-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830007628A true KR830007628A (ko) | 1983-11-04 |
| KR880001736B1 KR880001736B1 (ko) | 1988-09-10 |
Family
ID=10517217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810004348A KR880001736B1 (ko) | 1980-11-11 | 1981-11-10 | 2,4-디아미노-5(치환된)피리미딘의 제조방법 |
Country Status (35)
| Country | Link |
|---|---|
| US (4) | US4438267A (ko) |
| EP (1) | EP0051879B1 (ko) |
| JP (1) | JPS57114581A (ko) |
| KR (1) | KR880001736B1 (ko) |
| AR (1) | AR245447A1 (ko) |
| AU (1) | AU549449B2 (ko) |
| CA (1) | CA1186310A (ko) |
| CS (1) | CS273153B2 (ko) |
| CY (1) | CY1419A (ko) |
| DD (1) | DD201896A5 (ko) |
| DE (1) | DE3173752D1 (ko) |
| DK (1) | DK172884B1 (ko) |
| EG (1) | EG16107A (ko) |
| ES (5) | ES506969A0 (ko) |
| FI (1) | FI76333C (ko) |
| GB (1) | GB2087881B (ko) |
| GR (1) | GR81317B (ko) |
| HK (1) | HK23388A (ko) |
| HU (1) | HU188762B (ko) |
| IE (1) | IE52128B1 (ko) |
| IL (1) | IL64256A (ko) |
| IT (1) | IT1210589B (ko) |
| MC (1) | MC1418A1 (ko) |
| MY (1) | MY8600678A (ko) |
| NO (2) | NO160137C (ko) |
| NZ (1) | NZ198932A (ko) |
| PH (2) | PH25053A (ko) |
| PL (4) | PL139827B1 (ko) |
| PT (1) | PT73960B (ko) |
| RU (1) | RU1819264C (ko) |
| SG (1) | SG62686G (ko) |
| SU (4) | SU1424732A3 (ko) |
| YU (5) | YU42444B (ko) |
| ZA (1) | ZA817780B (ko) |
| ZM (1) | ZM9481A1 (ko) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4438267A (en) * | 1980-11-11 | 1984-03-20 | Daluge Susan M | Monoheteroring compounds and their use |
| ZA833067B (en) * | 1982-05-01 | 1984-12-24 | Wellcome Found | Antibacterial compounds |
| DK190983A (da) * | 1982-05-01 | 1983-11-02 | Wellcome Found | 2,4-diamino-5-(substituerede)pyrimidiner, fremgangsmaade til deres fremstilling og mellemprodukter derfor |
| US4590271A (en) * | 1982-05-01 | 1986-05-20 | Burroughs Wellcome Co. | 2,4-diamino-5-(substituted)pyrimidines, useful as antimicrobials |
| US4587341A (en) * | 1982-05-07 | 1986-05-06 | Burroughs Wellcome Co. | 2,4-diamino-5-(1,2,3,4-tetrahydro-(substituted or unsubstituted)-6-quinolylmethyl)pyrimidines, useful as antimicrobials |
| CA1244028A (en) * | 1983-04-14 | 1988-11-01 | Hans Maag | Pyrimidine derivatives |
| GB8603962D0 (en) * | 1986-02-18 | 1986-03-26 | Wellcome Found | Chemical compositions |
| GB8603964D0 (en) * | 1986-02-18 | 1986-03-26 | Cooper Animal Health Ltd | Compositions |
| LU86703A1 (fr) * | 1986-12-08 | 1988-07-14 | Oreal | Composition cosmetique photostable contenant un filtre uv-a et un filtre uv-b,son utilisation pour la protection de la peau contre les rayons uv et procede de stabilisation du filtre uv-a par le filtre uv-b |
| FI895821A0 (fi) * | 1988-12-07 | 1989-12-05 | Wellcome Found | Farmaceutiskt aktiva cns foereningar. |
| GB8903978D0 (en) * | 1989-02-22 | 1989-04-05 | Coopers Animal Health | Chemical compositions |
| GB9000241D0 (en) * | 1990-01-05 | 1990-03-07 | Coopers Animal Health | Pharmaceutical use |
| RU95113597A (ru) * | 1992-12-02 | 1997-06-10 | ФМК Корпорейшн (US) | Инсектицидная композиция, способы борьбы с насекомыми |
| US5707996A (en) * | 1995-11-06 | 1998-01-13 | Macleod Pharmaceuticals, Inc. | Pharmaceutical solution and methods for preparation thereof |
| DK0866791T3 (da) * | 1995-12-04 | 2002-04-22 | Arpida Ag | Diaminopyrimidiner, farmaceutiske præparater indeholdende disse og deres anvendelse som antibakterielle midler |
| WO2002010156A1 (en) * | 2000-07-29 | 2002-02-07 | Arpida Ag | Benzofuran derivatives and their use as antibacterial agents |
| ATE343415T1 (de) | 2001-06-29 | 2006-11-15 | Ab Science | Die verwendung von c-kit hemmer zur behandlung von entzündlichen darmerkrankungen |
| ATE330608T1 (de) * | 2001-06-29 | 2006-07-15 | Ab Science | Die verwendung von n-phenyl-2-pyrimidine-amine derivaten zur behandlung von entzündlichen erkrankungen |
| PT1401413E (pt) * | 2001-06-29 | 2007-02-28 | Ab Science | Uso de inibidores da tirosina cinase para tratar doenças alérgicas |
| JP2005500041A (ja) * | 2001-06-29 | 2005-01-06 | アブ サイエンス | 強力で選択的かつ非毒性のｃ−ｋｉｔ阻害剤 |
| CA2461181A1 (en) * | 2001-09-20 | 2003-05-01 | Ab Science | Use of potent, selective and non-toxic c-kit inhibitors for treating bacterial infections |
| CA2461182A1 (en) * | 2001-09-20 | 2003-05-01 | Ab Science | Use of tyrosine kinase inhibitors for promoting hair growth |
| JP2005511506A (ja) * | 2001-09-20 | 2005-04-28 | アブ サイエンス | 間質性膀胱炎を治療するための強力で選択的かつ非毒性のｃ−ｋｉｔ阻害剤の使用方法 |
| CN100443482C (zh) * | 2003-07-11 | 2008-12-17 | 阿皮德公开股份有限公司 | 苯并呋喃衍生物及其在制备治疗由细菌引起的感染的药物中的用途 |
| EE200700050A (et) * | 2005-02-18 | 2007-12-17 | Arpida Ag | Meetod bensofuraani valmistamiseks ning vahehendid |
| CN101253159B (zh) * | 2005-09-01 | 2011-12-07 | 弗·哈夫曼-拉罗切有限公司 | 作为p2x3和p2x2/3调节剂的二氨基嘧啶类化合物 |
| US20100029689A1 (en) * | 2008-07-02 | 2010-02-04 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors |
| JP5756096B2 (ja) * | 2009-06-12 | 2015-07-29 | ソックプラ−シアンセ エ ジェニー エス．ウ．セ． | グアニンリボスイッチ結合化合物及び抗生物質としてのその使用 |
| CN102649786B (zh) * | 2011-02-28 | 2014-08-27 | 郑州福源动物药业有限公司 | 一种2，4-二氨基-5-(8-二甲氨基-7-甲基-5-喹啉基甲基)-2，4-(1h，3h)嘧啶的制备方法 |
| CN103755684B (zh) * | 2014-02-10 | 2015-09-09 | 青岛蔚蓝生物股份有限公司 | 一种巴喹普林的制备方法 |
| JP2022535852A (ja) * | 2019-06-06 | 2022-08-10 | ベイジン タイド ファーマシューティカル カンパニー リミテッド | Ｐ２ｘ３及び／又はｐ２ｘ２／３受容体アンタゴニスト、それを含む医薬組成物及びその使用 |
| CN110818694B (zh) * | 2019-11-18 | 2023-04-21 | 上海医药工业研究院有限公司 | 艾拉普林中间体及其应用 |
| WO2022217295A1 (en) * | 2021-04-09 | 2022-10-13 | The Trustees Of The University Of Pennsylvania | Control of protein expression with tmp-protac compounds |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3049544A (en) * | 1962-08-14 | Method for the preparation of | ||
| DE1303727B (de) | 1959-09-03 | 1976-02-05 | Ausscheidung aus: 14 45 176 The Wellcome Foundation Ltd., London | Alpha-Arylidensubstituierte Propioni-Irile |
| US3956327A (en) * | 1969-03-06 | 1976-05-11 | Burroughs Wellcome Co. | Method of preparing 2,4-diamino-5-benzyl pyrimidines |
| BE792096A (fr) * | 1971-12-01 | 1973-05-30 | Hoffmann La Roche | Nouvelles benzylpyrimidines |
| GB1468374A (en) | 1974-03-06 | 1977-03-23 | Wellcome Found | Process for preparing a pyrimidine derivative |
| US4039543A (en) | 1974-12-24 | 1977-08-02 | Hoffmann-La Roche Inc. | Benzylpyrimidines |
| GB1582245A (en) * | 1976-06-09 | 1981-01-07 | Wellcome Found | Benzyl cyanoacetal derivatives and their conversion to pyrimidine derivatives |
| DE2730467A1 (de) * | 1977-07-06 | 1979-01-18 | Basf Ag | Benzylpyrimidine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| US4258045A (en) * | 1979-11-30 | 1981-03-24 | Merck & Co., Inc. | Inhibitor of dihydrofolate reductase |
| US4438267A (en) * | 1980-11-11 | 1984-03-20 | Daluge Susan M | Monoheteroring compounds and their use |
-
1981
- 1981-11-09 US US06/319,644 patent/US4438267A/en not_active Expired - Lifetime
- 1981-11-10 CS CS825781A patent/CS273153B2/cs unknown
- 1981-11-10 IE IE2631/81A patent/IE52128B1/en not_active IP Right Cessation
- 1981-11-10 SU SU813358051A patent/SU1424732A3/ru active
- 1981-11-10 GB GB8133833A patent/GB2087881B/en not_active Expired
- 1981-11-10 MC MC811560A patent/MC1418A1/xx unknown
- 1981-11-10 AU AU77334/81A patent/AU549449B2/en not_active Expired
- 1981-11-10 EG EG653/81A patent/EG16107A/xx active
- 1981-11-10 KR KR1019810004348A patent/KR880001736B1/ko active
- 1981-11-10 JP JP56180271A patent/JPS57114581A/ja active Granted
- 1981-11-10 PL PL1981239278A patent/PL139827B1/pl unknown
- 1981-11-10 PL PL1981239279A patent/PL139427B1/pl unknown
- 1981-11-10 NZ NZ198932A patent/NZ198932A/en unknown
- 1981-11-10 PL PL1981239280A patent/PL139828B1/pl unknown
- 1981-11-10 DK DK198104966A patent/DK172884B1/da active Protection Beyond IP Right Term
- 1981-11-10 DD DD81234745A patent/DD201896A5/de not_active IP Right Cessation
- 1981-11-10 HU HU813359A patent/HU188762B/hu unknown
- 1981-11-10 FI FI813546A patent/FI76333C/fi not_active IP Right Cessation
- 1981-11-10 ZA ZA817780A patent/ZA817780B/xx unknown
- 1981-11-10 GR GR66482A patent/GR81317B/el unknown
- 1981-11-10 IL IL64256A patent/IL64256A/xx not_active IP Right Cessation
- 1981-11-10 CA CA000389807A patent/CA1186310A/en not_active Expired
- 1981-11-10 PL PL1981233754A patent/PL139523B1/pl unknown
- 1981-11-10 NO NO813804A patent/NO160137C/no not_active IP Right Cessation
- 1981-11-10 IT IT8149676A patent/IT1210589B/it active
- 1981-11-10 ES ES506969A patent/ES506969A0/es active Granted
- 1981-11-10 YU YU2663/81A patent/YU42444B/xx unknown
- 1981-11-10 PT PT73960A patent/PT73960B/pt unknown
- 1981-11-11 DE DE8181109631T patent/DE3173752D1/de not_active Expired
- 1981-11-11 EP EP81109631A patent/EP0051879B1/en not_active Expired
- 1981-11-11 CY CY141981A patent/CY1419A/xx unknown
- 1981-11-11 ZM ZM94/81A patent/ZM9481A1/xx unknown
-
1983
- 1983-01-27 SU SU833543245A patent/SU1318148A3/ru active
- 1983-01-31 SU SU833547444A patent/SU1306473A3/ru active
- 1983-04-02 ES ES521203A patent/ES8405379A1/es not_active Expired
- 1983-04-02 ES ES521204A patent/ES8405380A1/es not_active Expired
- 1983-04-02 ES ES521202A patent/ES521202A0/es active Granted
- 1983-04-02 ES ES521201A patent/ES8405377A1/es not_active Expired
- 1983-09-07 PH PH29503A patent/PH25053A/en unknown
- 1983-09-07 PH PH29502A patent/PH22654A/en unknown
- 1983-10-03 YU YU01982/83A patent/YU198283A/xx unknown
- 1983-10-03 YU YU1983/83A patent/YU43551B/xx unknown
- 1983-10-03 YU YU01981/83A patent/YU198183A/xx unknown
- 1983-10-31 US US06/546,850 patent/US4587342A/en not_active Expired - Lifetime
- 1983-12-30 US US06/567,248 patent/US4603136A/en not_active Expired - Lifetime
-
1986
- 1986-02-02 RU SU863552053A patent/RU1819264C/ru active
- 1986-03-12 US US06/839,463 patent/US4761475A/en not_active Expired - Lifetime
- 1986-07-17 SG SG626/86A patent/SG62686G/en unknown
- 1986-12-30 MY MY678/86A patent/MY8600678A/xx unknown
-
1987
- 1987-01-14 SU SU874028793A patent/SU1535379A3/ru active
-
1988
- 1988-03-30 HK HK233/88A patent/HK23388A/xx not_active IP Right Cessation
- 1988-06-17 AR AR88311165A patent/AR245447A1/es active
- 1988-07-26 YU YU144288A patent/YU46697B/sh unknown
-
1994
- 1994-12-29 NO NO1994029C patent/NO1994029I1/no unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR830007628A (ko) | 2,4-디아미노-5(치환된)피리미딘의 제조방법 및 이것의 제약학적 조성물 | |
| US4644070A (en) | Chroman-3-ol compounds | |
| KR890005089A (ko) | 콜레스테롤 생합성의6-[[(치환된)피리딘-3-일]알킬]- 및 알켄일] 테트라하이드로-4-하이드록시피란-2-온 억제제 | |
| YU49235B (sh) | Novi derivati eritromicina, postupak za njihovo dobijanje i njihova primena kao medikamenata | |
| KR850002483A (ko) | 1-헤테로아릴-4-[(2,5-피롤리딘디온-1-일]피페라진 유도체의 제조방법 | |
| IE41539L (en) | Chroman derivatives. | |
| HUP9902340A2 (hu) | Kondenzált piridinek és pirimidinek aril-amino-származékai, eljárás előállításukra, valamint e vegyületeket tartalmazó gyógyászati készítmények, továbbá e vegyületek alkalmazása | |
| AU2482284A (en) | Imidazo-pyrimidine/pyridine derivatives | |
| KR870003100A (ko) | 벤즈이미다졸 유도체 | |
| ES8307760A1 (es) | Un procedimiento para la preparacion de derivados de 4-anilino-pirimidina. | |
| ES534505A0 (es) | Un procedimiento para la preparacion de compuestos de 1, 4-dihidropiridina | |
| CA2039039C (en) | Pyrimidine nucleoside derivative and antiviral agent containing the derivative as active ingredient | |
| IL63285A (en) | Phenylhydroxyalkyl-aminoalkyl-3,1-benzoxazin-2-one derivatives,their preparation and pharmaceutical compositions containing them | |
| KR850006194A (ko) | 치환된 벤조피란의 제조방법 | |
| KR920016421A (ko) | 피리딘 화합물 | |
| US3865827A (en) | Process for producing quanazolinone derivatives | |
| KR860700251A (ko) | 신규한 삼환성 또는 사환성 화합물 및 그 염류의 제조방법 | |
| ES8307221A1 (es) | "procedimiento para preparar derivados de dihidropiridina". | |
| IL64647A (en) | 2,8-disubstituted-4-thiomorpholino-pyrimido(5,4-d)pyrimidine derivatives,their preparation and pharmaceutical compositions containing them | |
| IE782028L (en) | Substituted furans | |
| KR880012594A (ko) | 벤조- 및 티에노-3,4-디하이드로-피리딘유도체, 이의 제조방법 및 이들 화합물을 함유하는 약제학적 조성물 | |
| KR840004731A (ko) | 2,4-디아미노-5-(치환된)피리미딘의 제조방법 | |
| KR860003222A (ko) | 1,4-디 하이드로피리딘-하이드록시아민의 제조방법 | |
| KR840003630A (ko) | 피리미돈 유도체 | |
| DE3363643D1 (en) | Basic substituted 4-phenyl-4,5,6,7-tetrahydrothieno(2,3-c) pyridines, process for their preparation and pharmaceutical compositions containing them |