CH641179A5 - Heterocyclische verbindungen mit stickstoff im ringsystem und verfahren zur herstellung derselben. - Google Patents

Heterocyclische verbindungen mit stickstoff im ringsystem und verfahren zur herstellung derselben. Download PDF

Info

Publication number: CH641179A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; oxo; general formula; methyl; pyrimidine
Prior art date: 1977-12-29

Application number

CH1323578A

Other languages

German (de)

English (en)

Inventor

Agnes Horvath

Istvan Hermecz

Zoltan Meszaros

Lelle Vasvari-Debreczy

Istvan Bitter

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

Priority date (The priority date 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 date listed.)

1977-12-29

Filing date

1978-12-28

Publication date

1984-02-15

1978-12-28 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1984-02-15 Publication of CH641179A5 publication Critical patent/CH641179A5/de

Links

238000000034 method Methods 0.000 title claims description 51
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims description 50
229910052757 nitrogen Inorganic materials 0.000 title claims description 39
-1 aminothiocarbonylamino Chemical group 0.000 claims description 123
150000001875 compounds Chemical class 0.000 claims description 103
239000011541 reaction mixture Substances 0.000 claims description 98
125000004432 carbon atom Chemical group C* 0.000 claims description 74
229910052739 hydrogen Inorganic materials 0.000 claims description 59
125000000217 alkyl group Chemical group 0.000 claims description 48
239000001257 hydrogen Substances 0.000 claims description 48
239000002904 solvent Substances 0.000 claims description 40
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 31
239000007858 starting material Substances 0.000 claims description 30
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 23
238000006243 chemical reaction Methods 0.000 claims description 22
125000004429 atom Chemical group 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 16
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 11
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
239000002841 Lewis acid Substances 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
150000007517 lewis acids Chemical class 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 10
239000012442 inert solvent Substances 0.000 claims description 9
150000008065 acid anhydrides Chemical class 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
150000001408 amides Chemical class 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
125000001072 heteroaryl group Chemical group 0.000 claims description 8
125000002619 bicyclic group Chemical group 0.000 claims description 7
150000004820 halides Chemical class 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
125000002950 monocyclic group Chemical group 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
150000007975 iminium salts Chemical class 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
150000001409 amidines Chemical class 0.000 claims description 5
125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
150000001450 anions Chemical group 0.000 claims description 4
ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 claims description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 claims description 3
HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 claims description 3
150000008282 halocarbons Chemical class 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
238000010952 in-situ formation Methods 0.000 claims 3
229910052801 chlorine Inorganic materials 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
239000004480 active ingredient Substances 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
229910021653 sulphate ion Inorganic materials 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 289
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 102
235000019441 ethanol Nutrition 0.000 description 99
239000000243 solution Substances 0.000 description 93
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 72
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 70
239000000047 product Substances 0.000 description 66
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 64
238000004458 analytical method Methods 0.000 description 64
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
238000001953 recrystallisation Methods 0.000 description 56
239000000155 melt Substances 0.000 description 53
239000013078 crystal Substances 0.000 description 48
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 41
229910000029 sodium carbonate Inorganic materials 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
238000002844 melting Methods 0.000 description 30
230000008018 melting Effects 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 24
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 21
239000005977 Ethylene Substances 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
238000001816 cooling Methods 0.000 description 18
239000000203 mixture Substances 0.000 description 16
VFMCUTPRJLZEEW-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine Chemical group C1=CC=CN2CC=CN=C21 VFMCUTPRJLZEEW-UHFFFAOYSA-N 0.000 description 13
239000012071 phase Substances 0.000 description 13
238000010992 reflux Methods 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 8
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
230000007935 neutral effect Effects 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
102100022404 E3 ubiquitin-protein ligase Midline-1 Human genes 0.000 description 6
101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
239000002178 crystalline material Substances 0.000 description 6
238000002955 isolation Methods 0.000 description 6
SOOUCPJOADTGKM-UHFFFAOYSA-N 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)N2C(C)CCCC2=N1 SOOUCPJOADTGKM-UHFFFAOYSA-N 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
238000004821 distillation Methods 0.000 description 5
239000002609 medium Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
JBZATZMJSINVNL-UHFFFAOYSA-N 9-(anilinomethylidene)-6-methyl-4-oxo-7,8-dihydro-6h-pyrido[1,2-a]pyrimidine-3-carbonitrile Chemical compound C12=NC=C(C#N)C(=O)N2C(C)CCC1=CNC1=CC=CC=C1 JBZATZMJSINVNL-UHFFFAOYSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
UBOXAHWUKQXQEH-UHFFFAOYSA-N 2,3,4,6-tetrahydro-1h-pyrido[1,2-a]pyrimidine Chemical compound C1=CCN2CCCNC2=C1 UBOXAHWUKQXQEH-UHFFFAOYSA-N 0.000 description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 3
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 2
FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 2
KOXNRJHZWXSKMF-UHFFFAOYSA-N 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C(C)CCCC2=N1 KOXNRJHZWXSKMF-UHFFFAOYSA-N 0.000 description 2
HCJOGZBBWGQKGC-UHFFFAOYSA-N 6-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC(=O)N2C(C)CCCC2=N1 HCJOGZBBWGQKGC-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
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 description 2
JLNGEXDJAQASHD-UHFFFAOYSA-N N,N-Diethylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=CC=C1 JLNGEXDJAQASHD-UHFFFAOYSA-N 0.000 description 2
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
HSSAXQPNRNFSLU-UHFFFAOYSA-N ethyl 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound C1CCC(C)N2C(=O)C(C(=O)OCC)=CN=C21 HSSAXQPNRNFSLU-UHFFFAOYSA-N 0.000 description 2
DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
229940067157 phenylhydrazine Drugs 0.000 description 2
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
WCVUTDNAIJJMSX-UHFFFAOYSA-N 2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound C1CCCC2=NC(C)=CC(=O)N21 WCVUTDNAIJJMSX-UHFFFAOYSA-N 0.000 description 1
LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 description 1
CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 description 1
QLENPRKQIFCBST-UHFFFAOYSA-N 3,6-dimethyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(C)C(=O)N2C(C)CCCC2=N1 QLENPRKQIFCBST-UHFFFAOYSA-N 0.000 description 1
HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
YKGILRCXDDGIMC-UHFFFAOYSA-N 3-ethyl-2,6-dimethyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound C1CCC(C)N2C(=O)C(CC)=C(C)N=C21 YKGILRCXDDGIMC-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
ZFCSEILWJVPZEZ-UHFFFAOYSA-N 4H-pyrido[1,2-a]pyrimidine pyrimidine Chemical compound C1=CN=CN=C1.C1=CC=CN2CC=CN=C21 ZFCSEILWJVPZEZ-UHFFFAOYSA-N 0.000 description 1
FPXDWQCNXFONMN-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=CC=CN2CC(C(=O)O)=CN=C21 FPXDWQCNXFONMN-UHFFFAOYSA-N 0.000 description 1
WJTGFDFDGZVNPV-UHFFFAOYSA-N 6,7,8,9-tetrahydro-4h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1CCCN2CC(C(=O)O)=CN=C21 WJTGFDFDGZVNPV-UHFFFAOYSA-N 0.000 description 1
LEPOWIGZXWVUIY-UHFFFAOYSA-N 6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound C1CCCN2C(=O)C=CN=C21 LEPOWIGZXWVUIY-UHFFFAOYSA-N 0.000 description 1
GRDANFRPPNRFBV-UHFFFAOYSA-N 6-methyl-2-phenyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound C1(=CC=CC=C1)C=1N=C2N(C(C=1)=O)C(CCC2)C GRDANFRPPNRFBV-UHFFFAOYSA-N 0.000 description 1
YUNQHMYCTXUCCF-UHFFFAOYSA-N 6-methyl-3-phenyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound O=C1N2C(C)CCCC2=NC=C1C1=CC=CC=C1 YUNQHMYCTXUCCF-UHFFFAOYSA-N 0.000 description 1
NJHBEMSRPZEWAT-UHFFFAOYSA-N 6-methyl-4-oxo-1,6,7,8-tetrahydropyrido[1,2-a]pyrimidine-9-carbaldehyde Chemical compound N1C=CC(=O)N2C(C)CCC(C=O)=C21 NJHBEMSRPZEWAT-UHFFFAOYSA-N 0.000 description 1
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
229910021576 Iron(III) bromide Inorganic materials 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
NRFMEFUUIQAJGM-UHFFFAOYSA-N N1C=2N(CCC1)CC=CC2.N2=C1N(CC=C2)C=CC=C1 Chemical compound N1C=2N(CCC1)CC=CC2.N2=C1N(CC=C2)C=CC=C1 NRFMEFUUIQAJGM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
101150052863 THY1 gene Proteins 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
JTXJZBMXQMTSQN-UHFFFAOYSA-N amino hydrogen carbonate Chemical compound NOC(O)=O JTXJZBMXQMTSQN-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical group NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
WADSLQQIOJIXTB-UHFFFAOYSA-L dichloroalumane Chemical compound Cl[AlH]Cl WADSLQQIOJIXTB-UHFFFAOYSA-L 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000007336 electrophilic substitution reaction Methods 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
GVEKOTSOWVJLFX-UHFFFAOYSA-N ethyl 2-(6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-3-yl)acetate Chemical compound C1CCC(C)N2C(=O)C(CC(=O)OCC)=CN=C21 GVEKOTSOWVJLFX-UHFFFAOYSA-N 0.000 description 1
GRBTZPKCTXIBMP-UHFFFAOYSA-N ethyl 4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound C1CCCN2C(=O)C(C(=O)OCC)=CN=C21 GRBTZPKCTXIBMP-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000005597 hydrazone group Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NWHUWTFLOIGXEA-UHFFFAOYSA-N methyl 6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound C1CCC(C)N2C(=O)C(C(=O)OC)=CN=C21 NWHUWTFLOIGXEA-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
ZQUVDXMUKIVNOW-UHFFFAOYSA-N n,n'-diphenylmethanimidamide Chemical compound C=1C=CC=CC=1NC=NC1=CC=CC=C1 ZQUVDXMUKIVNOW-UHFFFAOYSA-N 0.000 description 1
APUCQYMTNZQNDR-UHFFFAOYSA-N n,n-dimethylazete-2-carboxamide Chemical compound CN(C)C(=O)C1=NC=C1 APUCQYMTNZQNDR-UHFFFAOYSA-N 0.000 description 1
KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001151 other effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
MVJKXJPDBTXECY-UHFFFAOYSA-N trifluoroborane;hydrate Chemical compound O.FB(F)F MVJKXJPDBTXECY-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Cardiology (AREA)
Pulmonology (AREA)
Heart & Thoracic Surgery (AREA)
Anesthesiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Indole Compounds (AREA)

CH1323578A 1977-12-29 1978-12-28 Heterocyclische verbindungen mit stickstoff im ringsystem und verfahren zur herstellung derselben. CH641179A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU77CI1792A HU184058B (en)	1977-12-29	1977-12-29	Process for preparing new compounds with nitrogen bridge head

Publications (1)

Publication Number	Publication Date
CH641179A5 true CH641179A5 (de)	1984-02-15

Family

ID=10994681

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1323578A CH641179A5 (de)	1977-12-29	1978-12-28	Heterocyclische verbindungen mit stickstoff im ringsystem und verfahren zur herstellung derselben.

Country Status (8)

Country	Link
JP (1)	JPS54109997A (fr)
BE (1)	BE873192A (fr)
CH (1)	CH641179A5 (fr)
DE (1)	DE2854114A1 (fr)
FR (1)	FR2413387A1 (fr)
GB (1)	GB2011407B (fr)
HU (1)	HU184058B (fr)
SU (2)	SU1181546A3 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL59802A (en)	1979-05-08	1983-07-31	Erba Farmitalia	Substituted pyrido(1,2-a)pyrimidine carboxylic acid derivatives,their preparation and pharmaceutical compositions containing them
JPS62242682A (ja) *	1986-04-16	1987-10-23	Tokyo Tanabe Co Ltd	新規なピリド［１，２―ａ］ピリミジン誘導体及びその製造法
AR046938A1 (es) *	2003-12-12	2006-01-04	Merck & Co Inc	Procedimiento para preparar hexahidropirimido[1,2-a]azepin-2-carboxilatos y compuetos similares

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU174693B (hu) *	1976-02-12	1980-03-28	Chinoin Gyogyszer Es Vegyeszet	Sposob poluchenija kondensirovannykh proizvodnykh pirimidina

1977
- 1977-12-29 HU HU77CI1792A patent/HU184058B/hu unknown
1978
- 1978-12-15 DE DE19782854114 patent/DE2854114A1/de not_active Ceased
- 1978-12-27 FR FR7836459A patent/FR2413387A1/fr active Granted
- 1978-12-28 GB GB7850105A patent/GB2011407B/en not_active Expired
- 1978-12-28 CH CH1323578A patent/CH641179A5/de not_active IP Right Cessation
- 1978-12-28 SU SU782704101A patent/SU1181546A3/ru active
- 1978-12-29 JP JP16460378A patent/JPS54109997A/ja active Pending
- 1978-12-29 BE BE192657A patent/BE873192A/fr not_active IP Right Cessation
1982
- 1982-12-16 SU SU823522507A patent/SU1245260A3/ru active

Also Published As

Publication number	Publication date
FR2413387A1 (fr)	1979-07-27
FR2413387B1 (fr)	1982-10-29
GB2011407A (en)	1979-07-11
BE873192A (fr)	1979-04-17
HU184058B (en)	1984-06-28
GB2011407B (en)	1982-09-08
DE2854114A1 (de)	1979-07-12
JPS54109997A (en)	1979-08-29
SU1181546A3 (ru)	1985-09-23
SU1245260A3 (ru)	1986-07-15

Legal Events

Date	Code	Title	Description
1987-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE69013607T2 (de)	1995-03-02	Pyrazol-Derivate, Verfahren zu deren Herstellung und Anwendung.
DE3780263T2 (de)	1992-12-24	Imidazopyridinverbindungen und verfahren zu ihrer herstellung.
DE68913831T2 (de)	1994-06-30	Kondensierte Pyrimidinderivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen.
EP0726899B1 (fr)	2000-01-19	Nouveaux derives de pyrazinecarboxamide, leur preparation et leur utilisation dans des medicaments
DD161210A5 (de)	1985-06-12	Verfahren zur herstellung neuer 3-substituierter beta-carboline
US3303199A (en)	1967-02-07	Certain imidazolone derivatives and process for making same
NZ207156A (en)	1987-07-31	(2 quinazolinyl)-oxalkylamide derivatives and pharmaceutical compositions
EP0005205A1 (fr)	1979-11-14	5.6-Diméthylpyrrolo(2,3-d)pyrimidines substituées, leur procédé de préparation et médicamentsles contenant
US4219649A (en)	1980-08-26	Pyrido[1,2-a]pyrimidine derivatives
US4782055A (en)	1988-11-01	Imidazopyridine compounds useful in the treatment of ulcers
DD224851A5 (de)	1985-07-17	Verfahren zur herstellung von imidazolen
EP0058341A1 (fr)	1982-08-25	Dérivés de l'azépine, leur préparation et médicaments les contenant
US5387588A (en)	1995-02-07	Pyridopyrimidine derivatives, pharmaceutical compositions containing them and process for preparing same
DE3587362T2 (de)	1993-09-09	Benzo-kondensierte heterocyclische verbindung.
DE3146599A1 (de)	1983-07-07	Neue triazolochinazoline, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen
CH641179A5 (de)	1984-02-15	Heterocyclische verbindungen mit stickstoff im ringsystem und verfahren zur herstellung derselben.
FI71560C (fi)	1987-01-19	Foerfarande foer framstaellning av nya analgetiska, antiflogistiska och antipyretiska 1,4,9,10-tetrahydropyrazolo -/4,3-e/pyrido/3,2-b//1,4/diazepin-10-oner.
US5158951A (en)	1992-10-27	Pyridopyrimidine derivatives useful in treatment of ulcers
US4048184A (en)	1977-09-13	6-Phenyl-2H-pyrazolo[3,4-b]pyridines
CH638207A5 (de)	1983-09-15	2,3-polymethylen-4-oxo-4h-pyrido(1,2-a)pyrimidin verbindungen und tetrahydro- oder octahydro-derivaten desselben, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate.
DE3017625A1 (de)	1980-11-20	Verfahren zur herstellung von 3-substituierten tetrahydro-pyrrolo eckige klammer auf 1,2-a eckige klammer zu pyrimidinen und die verbindungen enthaltende pharmazeutische praeparate sowie neue 3-substituierte-tetrahydro-pyrrolo eckige klammer auf 1,2-a eckige klammer zu pyrimidine
GB1597091A (en)	1981-09-03	Pyrazolopyridines
DD150605A5 (de)	1981-09-09	Verfahren zur herstellung dihalogen-substituierter kondensierter pyrimidin-4-on-derivate
DD220307A5 (de)	1985-03-27	Verfahren zur herstellung von polycyclische carbonsaeureverbindungen
CA1262545A (fr)	1989-10-31	Imidazo-isoquinoleines et imidazothienopyridines