KR0177294B1 - 피리미딘 유도체의 제조방법 - Google Patents
피리미딘 유도체의 제조방법 Download PDFInfo
- Publication number
- KR0177294B1 KR0177294B1 KR1019960014538A KR19960014538A KR0177294B1 KR 0177294 B1 KR0177294 B1 KR 0177294B1 KR 1019960014538 A KR1019960014538 A KR 1019960014538A KR 19960014538 A KR19960014538 A KR 19960014538A KR 0177294 B1 KR0177294 B1 KR 0177294B1
- Authority
- KR
- South Korea
- Prior art keywords
- fluorophenylamino
- methyl
- dimethyl
- tetrahydroisoquinolin
- added
- Prior art date
- 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 - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- QPILYVQSKNWRDD-UHFFFAOYSA-N 1-methyl-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2C(C)NCCC2=C1 QPILYVQSKNWRDD-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- -1 5,6-dimethyl-2- (4-fluorophenylamino) -4- (1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl) pyridine hydrochloride Chemical compound 0.000 claims abstract description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- MALPZYQJEDBIAK-UHFFFAOYSA-N n-(4-fluorophenyl)-4,5-dimethyl-6-(1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyrimidin-2-amine;hydron;chloride Chemical compound Cl.C1CC2=CC=CC=C2C(C)N1C(C(=C(C)N=1)C)=NC=1NC1=CC=C(F)C=C1 MALPZYQJEDBIAK-UHFFFAOYSA-N 0.000 claims description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims description 5
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- BJWVXNKERMIEBG-UHFFFAOYSA-N 1-methyl-2-pyrimidin-4-yl-3,4-dihydro-1H-isoquinoline hydrochloride Chemical compound Cl.CC1N(CCC2=CC=CC=C12)C1=NC=NC=C1 BJWVXNKERMIEBG-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 150000002367 halogens Chemical class 0.000 abstract description 4
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 102100021904 Potassium-transporting ATPase alpha chain 1 Human genes 0.000 abstract description 2
- 108010083204 Proton Pumps Proteins 0.000 abstract description 2
- 239000003699 antiulcer agent Substances 0.000 abstract description 2
- 230000027119 gastric acid secretion Effects 0.000 abstract description 2
- 230000002441 reversible effect Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- ABZSCKQLFVOMNZ-UHFFFAOYSA-N 2-(4-fluoroanilino)-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound O=C1C(C)=C(C)NC(NC=2C=CC(F)=CC=2)=N1 ABZSCKQLFVOMNZ-UHFFFAOYSA-N 0.000 description 7
- GXCRXDFXVDTHGZ-UHFFFAOYSA-N 4-chloro-n-(4-fluorophenyl)-5,6-dimethylpyrimidin-2-amine Chemical compound ClC1=C(C)C(C)=NC(NC=2C=CC(F)=CC=2)=N1 GXCRXDFXVDTHGZ-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- WPNKMXLMLBKXLP-UHFFFAOYSA-N 1-methyl-2-pyrimidin-2-yl-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2C(C)N1C1=NC=CC=N1 WPNKMXLMLBKXLP-UHFFFAOYSA-N 0.000 description 3
- APYNFQKDQSLCOA-UHFFFAOYSA-N 4-bromo-n-(4-fluorophenyl)-5,6-dimethylpyrimidin-2-amine Chemical compound BrC1=C(C)C(C)=NC(NC=2C=CC(F)=CC=2)=N1 APYNFQKDQSLCOA-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LLADPGXAIXIKNJ-UHFFFAOYSA-N carbonic acid;2-(4-fluorophenyl)guanidine Chemical compound OC(O)=O.NC(N)=NC1=CC=C(F)C=C1 LLADPGXAIXIKNJ-UHFFFAOYSA-N 0.000 description 3
- FNENWZWNOPCZGK-UHFFFAOYSA-N ethyl 2-methyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)C(C)=O FNENWZWNOPCZGK-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- WBXGWHOXLHBKAO-UHFFFAOYSA-N N-(4-fluorophenyl)-4-(1-methyl-3,4-dihydro-1H-isoquinolin-2-yl)pyrimidin-2-amine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)NC1=NC=CC(=N1)N1C(C2=CC=CC=C2CC1)C WBXGWHOXLHBKAO-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- LECZXZOBEZITCL-UHFFFAOYSA-N revaprazan Chemical compound C1CC2=CC=CC=C2C(C)N1C(C(=C(C)N=1)C)=NC=1NC1=CC=C(F)C=C1 LECZXZOBEZITCL-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000010792 warming Methods 0.000 description 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
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019960014538A KR0177294B1 (ko) | 1996-05-04 | 1996-05-04 | 피리미딘 유도체의 제조방법 |
| IN1094DE1997 IN186440B (enrdf_load_stackoverflow) | 1996-05-04 | 1997-04-29 | |
| DK97920966T DK0900214T3 (da) | 1996-05-04 | 1997-04-30 | Fremgangsmåde til fremstilling af pyrmidin-derivater |
| ES97920966T ES2165052T3 (es) | 1996-05-04 | 1997-04-30 | Procedimiento para la preparacion de derivados de pirimidina. |
| EP97920966A EP0900214B1 (en) | 1996-05-04 | 1997-04-30 | Process for preparation of pyrimidine derivatives |
| RU98121687/04A RU2174978C2 (ru) | 1996-05-04 | 1997-04-30 | Способ получения производных пиримидина, промежуточные продукты и способ их получения |
| JP53975697A JP3160297B2 (ja) | 1996-05-04 | 1997-04-30 | ピリミジン誘導体の製造方法 |
| CN97194367A CN1097591C (zh) | 1996-05-04 | 1997-04-30 | 制备嘧啶衍生物的方法 |
| DE69706981T DE69706981T2 (de) | 1996-05-04 | 1997-04-30 | Verfahren zur herstellung von pyrimidin-derivaten |
| AT97920966T ATE206117T1 (de) | 1996-05-04 | 1997-04-30 | Verfahren zur herstellung von pyrimidin-derivaten |
| AU27133/97A AU712970B2 (en) | 1996-05-04 | 1997-04-30 | Process for preparation of pyrimidine derivatives |
| PT97920966T PT900214E (pt) | 1996-05-04 | 1997-04-30 | Processo para a preparacao de derivados da pirimidina |
| US09/171,579 US5990311A (en) | 1996-05-04 | 1997-04-30 | Process for preparation of pyrimidine derivatives |
| CA002253906A CA2253906C (en) | 1996-05-04 | 1997-04-30 | Process for preparation of pyrimidine derivatives |
| CA002358479A CA2358479C (en) | 1996-05-04 | 1997-04-30 | 4-substituted-2-(4-fluorophenylamino)-5,6 dimethylpyrimidine |
| HK99104379.5A HK1019336B (en) | 1996-05-04 | 1997-04-30 | Process for preparation of pyrimidine derivatives |
| PCT/KR1997/000073 WO1997042186A1 (en) | 1996-05-04 | 1997-04-30 | Process for preparation of pyrimidine derivatives |
| CNB021247854A CN1190427C (zh) | 1996-05-04 | 1997-04-30 | 制备嘧啶衍生物的方法 |
| JP2000198538A JP2001055379A (ja) | 1996-05-04 | 2000-06-30 | １−メチル−１，２，３，４−テトラヒドロイソキノリンの製造方法 |
| US09/667,428 US6252076B1 (en) | 1996-05-04 | 2000-09-21 | Process for preparation of pyrimidine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019960014538A KR0177294B1 (ko) | 1996-05-04 | 1996-05-04 | 피리미딘 유도체의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR970074778A KR970074778A (ko) | 1997-12-10 |
| KR0177294B1 true KR0177294B1 (ko) | 1999-03-20 |
Family
ID=19457730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019960014538A Expired - Lifetime KR0177294B1 (ko) | 1996-05-04 | 1996-05-04 | 피리미딘 유도체의 제조방법 |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR0177294B1 (enrdf_load_stackoverflow) |
| IN (1) | IN186440B (enrdf_load_stackoverflow) |
-
1996
- 1996-05-04 KR KR1019960014538A patent/KR0177294B1/ko not_active Expired - Lifetime
-
1997
- 1997-04-29 IN IN1094DE1997 patent/IN186440B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR970074778A (ko) | 1997-12-10 |
| IN186440B (enrdf_load_stackoverflow) | 2001-09-01 |
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