PL125789B1 - Process for preparing novel derivatives of quinazoline - Google Patents
Process for preparing novel derivatives of quinazoline Download PDFInfo
- Publication number
- PL125789B1 PL125789B1 PL1980221249A PL22124980A PL125789B1 PL 125789 B1 PL125789 B1 PL 125789B1 PL 1980221249 A PL1980221249 A PL 1980221249A PL 22124980 A PL22124980 A PL 22124980A PL 125789 B1 PL125789 B1 PL 125789B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- group
- radical
- alk
- radicals
- Prior art date
Links
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title claims abstract 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract 9
- 125000001424 substituent group Chemical group 0.000 claims abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 4
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 2
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 2
- 125000001544 thienyl group Chemical group 0.000 claims abstract 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- -1 alkyl radicals Chemical class 0.000 claims 13
- 150000003254 radicals Chemical class 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 5
- 150000005840 aryl radicals Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- AHMIRVCNZZUANP-LPBAWZRYSA-N chrysalin Chemical compound CC(O)=O.CC(O)=O.C([C@@H](C(=O)N[C@@H](C(C)C)C(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](C)N)C1=CC=CC=C1.C([C@@H](C(=O)N[C@@H](C(C)C)C(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](C)N)C1=CC=CC=C1.C([C@@H](C(=O)N[C@@H](C(C)C)C(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](C)N)C1=CC=CC=C1 AHMIRVCNZZUANP-LPBAWZRYSA-N 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 108010018091 rusalatide acetate Proteins 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 229940076279 serotonin Drugs 0.000 abstract 1
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 241000566576 Tyto Species 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
»lPc- rydynyflo/-*fletaffiOTiu, 8 czesci weglanu sodowego i 1120 czesci ^Hmetyflopentanottu-ia utrzymuje sie w 45 stanie ^wrzenia pod chlodnica zwrotna z oddziela¬ czem iwody i po upiywSe 112 godzin odsacza sie wyittworzony osad i przekrytsbaiizowujle go z 96 czesci propanolu-2. Otrzymuje sie 3 czesci 2-tf3- ¦ nyflo]^tyto}-4/3IH/-cllxiiziazoai'nonu o temperaturze tcptanenda O09U9°1C.?W analogiczny sposób wytwarza sie nastejpujace zwiafzki: sól 2WzMcMoroJ!enylo/^-{2^ 55 ^iperydynyaolH^ylo}^/3H/Hc*inazo sem /E/n2-ibuftJenoowtukarboikteyiowyffn <1:1) o tetm- peratuiae topnienia .1A9J2PC <3fl»/» wydajnosci teo- retycznejf), sól 0-ite-diBorotfenylo/*{te w -piperydymyflo]-etylo}-fc^/-^ z kwa¬ sem ^-^-buitenc^wUkarhoksylowysn peratonze topnienia aa5,«°C retycznej) i ból 9-{|2^4r^l4Hrluorolbenzoilo/-l^pdpery- dytaylo]-etyl*}^-dflenyfliomietyao/^^ « z kwasem /E/-24jutenodwufcaribofcsylo^ (1:1) o teimperaturze topnienia 22tiftC (filF/t wydajnosci teoretycznej). PL PL
Claims (2)
1. Zastrzezenia patentowe H. Stposób wytwarzania nowych pochodnych chi- nazoliiny o ogólnym wzorze II, w którym Ar ozna¬ cza rodnik arydowy, X oznacza grupe =C=0, =OHIOH luib =(GHflj, R oznacza atom wodoru lub nizszy rodnik adkilowy, Alk oznacza lancuch alki- lenowy o 1—4 atomach wegla* a Q oznfeucza rodnik dhonazollinylotwy polaczony w pozycjd \L&& lub 4 z aikilenowym lancuchem bocznym i zawierajacy co najmniej jedna grupe karbonylowa lub tiokar- bolnylowa,' przy czym pierscien benzenowym tego rodnika chinazolinylowego ma ewenitualnde !•, 2 lub 3 podstaiwndki jiedniakiowe knb rózne,, takie jak atomy Chlorowców, nizsze rodniki alkilowe, nizsze rodntikd alkotesydowe, grupy tróJfluoTometyiowe, nitrowe i cyjanowe, a pierscien pdrymfidynowy te¬ go rodbdka chdnazolinylowego moze byc czesciowo lub calkowicie nasycony i moze ewentuaOnle za¬ wierac Hi, I2f lub 3 podstaiwnjki jednakowe lub róz¬ ne* takie jak nizsze rodniki aWowe, rodnikti ary- lowe i rodniki aryloallkilowe o nizszym rodniku aMlowytm, przy czym okreslenie ^rodnik aryao- w^ uzyte w odniesieniu do symbolu Ar i sym- bofbu Q oznacza rodnik flemyiLowy, tienylowy i pi- rydylowy albo rodnik toiylowy zawierajacy 1, 2 Lub 3 jednakowe luib rózne podstawniki, takie jak atomy chlorowców, nizsze rodniki alkilowe, nizsza rodniki alkoksyllowei, grupy trójtfauoroniietylowe i grupy afmtinowe, jak równiez £arniakoQoi^cznie db- puszczallnych soli addycyjnych zwiazków o wzorze 1 z kwasami, znamienny tym, ze zwiazek o wzo¬ rze 4* w którym AUk i Q maja wyzej podane zna¬ czenie,, a W oznacza zdolna do reakcji grupe es^ trawa, taka jak atom chlorowca lub grupa sulfo- nyfloksylowa, zwlaszcza niety^osultfonylloksylowa lub 4-anetylofenyaoisuIfonyloksyIowa, poddaje sie w srodowisku obojejtneigo rozpuszczallnika, w pod¬ wyzszonej temperaturze i w obecnosci zasady re- akcjfi ze zwiazkiem o wzorze 5, w 'którym R, X i Ar onaja wyzej podlane znaczenie, po czym otrzy¬ many zwiazek o wzorze «1 ewentualnie przeprowa¬ dza sie w dopuszczalna (farmakologicznie sól addy¬ cyjna z kwasem.
2. Sposób wedlug zastrz. 1, inamJenny tym, ze 3-/2^hlóroetyló/-l^llE]1^H/Hcn^ poddaje sie reakcjii z chlorowodorkliem i^Hffluorofenylo/-/4- Hpiperydynylo/-^metanonu i wytworzony 3-{l2-F4-te- 4fli^obenzoiao/ipiperydynyao]-etyao}-^ HchJnazolinodion ewenitualniie przeprowadza sie w farmakologicznie dopuszczalna sól addycyjna z kwasem. 13. Sposób wytwarzania nowych pochodnych chi- nazoliny o ogólnym wzorze 11, w którym Air ozna¬ cza rodnik arylowy, X oznacza grupe =CX)-nizszy alkil/i, grupe =C=NlOH, grupe =C=(N1—NH^ gru¬ pe o wzorze (21, w któryim Ra oznacza altwm wo¬ doru lub nizszy rodnik alkilowy, albo X oznacza grape o wzorze 3, w którym q oznacza liczbe cal¬ kowita a albo 3; R oznacza atom wodoru/ grupe17 125 789 18 hydroksylowa lub nlizlsizy rodnik alkilowy, ponzy ozym .gidy R oznacza grupe hydroksylowa wóiw- ozais X imoze rówoieiz oznaczac girupe =C=0, gru¬ pe =IOH]OH lub grupe =CHa, Alk oizjnacza lan- ouclh allkilenowy o li-^l atomach wegla, a Q ozna¬ cza rodnik chinazolihylowy polaczony w pozycjii ly2,QI iluto 4 z aflkiilanowym lancuichelm bocznym i zawierajacy co najmniej jedna girupe karibony- lowa luib tiokarbonylowa, pirzy ozym pierscien benzenowy tego rodnika chinaizoLinylowego ma ewentualnie 1, 2 luib 3 podstawniki jednakowe Lub rózne, (takie jak atomy chlorowców., nizsze rodniki alkilowe,, nizsze rodniki alkoksylowe,, grupy tonóij- filuoroimietylowe, nitrowe d cyjanowe, a pierscien piryimiidynowy tego rodnika chinaizolinylowelgo moze byc lozesciowo llulb calkowicie nasycony i moze ewentualnie izawierac U, 12 luib 3 podstawniki jednakowe Hub rózne, takie jak miizfsize rodniki al¬ kilowe, rodnliki aryilowe i rodmdki aryloalkilowe o nizszym rodniku alkilowym,, (przy czym okresle¬ nie „rodnik arylowy" uzyte w odiniiefeiieniu do sym- 10 15 20 bolu Air d syimibolu Q oznacza rodnik iflenylowy, tienylowy d pirydylowy albo rodnik fenylowy za¬ wierajacy 1, 2 lub S jednakowe luib rózne pod¬ stawniki, ftakde jak aitomy idhiorowiców, nizsze rod¬ niki alkilowe, nizsze rodmdki alkoksylowe, grupy trójiflluioromeitylowe d grupy aminowe, jak równiez farmakologicznie dopuszczalnych soli addycyjnych zwiazków o wzorze 1 z kwasami, znamienny tym, ze zwiazek o wizotrze 4, w którym Alk i Q maja wyzej podane znaczenie, a W -oiznaicza zdolna do reakcjii grupe es«trowa, "taka jiak atom chlorowca lub grupa suUfonyloksylowa, izwlalstzcza im!eltylosul- fonyl'oksylowa lub 4nmeityloifenylosuliionylloklsylolwa, poddaje sie w srodowisku obojetnego rozpuszczal¬ nika, w podwyzsizoneij telm|peratuirze i w obecnosci zasady reakcjii ze zwiazkiem o wizorze 5, w ttdtó- rym K,, X i Ar imaja wyzej podane znaczenie, po czym otrzymany izwiazek o wzorze H ewentualnie przeprowadza iaie w diopuB|zczalna farmakoloigicznie sól addycyjna iz kwasem. R Q-Alk-NYx-Ar Wzórl X-Ar WzoMc125 789 N-Alk-N V Wzór 1d N-Alk-N WzóMe / O II C-Ar O ii C-Ar N-Alk-N \ O ii CH-O-C-R, Wzór 2 Wzór 3 Q—Alk—W Wzór 4 R I HN~_Vx -Ar Wzór 5 R i Z-NVx-Ar Wzór 9125 789 R' Q-Alk-OH estryfikacja Z-N O ii C-Ar Wzór 9a Schemat 3 Wzór 6 cyklizacja Q-Alk-W l Wzór U cyklizacja g-Alk-OH "**+. gHUk-W Wzór 7 Wzór 8 Z-N R Schemat 1 I H + Wzór 10 NC-CH2-Ar zasqdQ Wzór 11 Z-N / CN C-Ar Wzór 12 R' katalityczne uwodornienie R CN :-N^CH - Ar Wzór 13 utlenianie Z-Ny-Mg-halo + ArCN 1 ° z-K ii Z-N^^-C-Ar -»¦ Wzór 9a Schemat 2 Wzór 14 Wzór 15 PL PL
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US149379A | 1979-01-08 | 1979-01-08 | |
| US06/084,272 US4335127A (en) | 1979-01-08 | 1979-10-12 | Piperidinylalkyl quinazoline compounds, composition and method of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL221249A1 PL221249A1 (pl) | 1980-12-01 |
| PL125789B1 true PL125789B1 (en) | 1983-06-30 |
Family
ID=26669096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1980221249A PL125789B1 (en) | 1979-01-08 | 1980-01-07 | Process for preparing novel derivatives of quinazoline |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4335127A (pl) |
| EP (1) | EP0013612B1 (pl) |
| JP (1) | JPS55105679A (pl) |
| KR (3) | KR850000684B1 (pl) |
| AT (1) | ATE5258T1 (pl) |
| AU (1) | AU536175B2 (pl) |
| CA (1) | CA1132557A (pl) |
| CS (1) | CS223977B2 (pl) |
| CY (1) | CY1252A (pl) |
| DE (1) | DE3065489D1 (pl) |
| DK (1) | DK170669B1 (pl) |
| ES (1) | ES8101586A1 (pl) |
| FI (1) | FI66609C (pl) |
| GR (1) | GR67304B (pl) |
| HK (1) | HK76284A (pl) |
| HU (1) | HU184222B (pl) |
| IE (1) | IE49351B1 (pl) |
| IL (1) | IL59084A (pl) |
| LU (1) | LU88219I2 (pl) |
| MA (1) | MA18694A1 (pl) |
| MY (1) | MY8700555A (pl) |
| NL (1) | NL930018I2 (pl) |
| NO (1) | NO155243C (pl) |
| NZ (1) | NZ192551A (pl) |
| PH (1) | PH17114A (pl) |
| PL (1) | PL125789B1 (pl) |
| PT (1) | PT70662A (pl) |
| RO (1) | RO79148A (pl) |
| SG (1) | SG48684G (pl) |
| SU (1) | SU1041034A3 (pl) |
| YU (1) | YU42957B (pl) |
| ZA (1) | ZA8082B (pl) |
Families Citing this family (112)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA806501B (en) * | 1979-10-27 | 1981-10-28 | Richardson Merrell Inc | 4-(4-alkyl-aroyl-1-piperidino)butyrophenone antipsychotic agents |
| CA1183847A (en) * | 1981-10-01 | 1985-03-12 | Georges Van Daele | N-(3-hydroxy-4-piperidinyl)benzamide derivatives |
| US4355037A (en) * | 1981-11-12 | 1982-10-19 | Hoechst-Roussel Pharmaceuticals | 3-(4-Piperidyl)-1,2-benzisoxales |
| ZA841728B (en) * | 1983-03-09 | 1984-11-28 | Ciba Geigy Ag | Novel carboxamides |
| DK159420C (da) * | 1983-03-09 | 1991-03-11 | Ciba Geigy Ag | N-(piperidinyl-alkyl)-carboxamider og salte deraf, farmaceutiske praeparater indeholdende disse forbindelser samt anvendelsen af forbindelserne til fremstilling af antipsykotiske farmaceutiske praeparater |
| JPS608274A (ja) * | 1983-06-27 | 1985-01-17 | Fujisawa Pharmaceut Co Ltd | 新規キナゾリノン誘導体およびその製造法・並びに抗アレルギ−剤 |
| PH23995A (en) * | 1984-01-09 | 1990-02-09 | Janssen Pharmaceutica Nv | 4((bicycle heterocyclyl)-methyl and hetero)piperidines |
| CS247557B1 (en) * | 1984-04-06 | 1987-01-15 | Ludmila Fisnerova | Esters of 3-(2-hydroxyethyl)-4(3h)-quinazolinone |
| EP0177078A1 (en) * | 1984-09-12 | 1986-04-09 | Duphar International Research B.V | Spasmolytically active tertiary amine derivatives and method of preparing the same |
| US4634769A (en) * | 1984-09-25 | 1987-01-06 | Ortho Pharmaceutical Corporation | Process for the preparation of 8-halo-5,6-dialkoxyquinazoline-2,4-diones and their salts |
| US4665075A (en) * | 1984-12-05 | 1987-05-12 | Janssen Pharmaceutica N.V. | Derivatives of hydroxy- or amino-substituted (piperidinylalkyl)quinazolines |
| CA1246074A (en) * | 1984-12-05 | 1988-12-06 | Albertus H.M.T. Van Heertum | Derivatives of hydroxy- or amino-substituted (piperidinylalkyl)quinazolines |
| US4804663A (en) * | 1985-03-27 | 1989-02-14 | Janssen Pharmaceutica N.V. | 3-piperidinyl-substituted 1,2-benzisoxazoles and 1,2-benzisothiazoles |
| JPH0615529B2 (ja) * | 1985-04-01 | 1994-03-02 | エーザイ株式会社 | 新規ピペリジン誘導体 |
| FR2581993B1 (fr) * | 1985-05-14 | 1988-03-18 | Synthelabo | Derives de (benzoyl-4 piperidino)-2 phenyl-1 alcanols, leur preparation et leur application en therapeutique |
| US4753944A (en) * | 1985-11-04 | 1988-06-28 | American Cyanamid Company | Pharmaceutical methods of using 3-heteroarylalkyl-4-quinazolinones |
| US4710502A (en) * | 1985-11-04 | 1987-12-01 | American Cyanamid Company | 3-heteroarylalkyl-4-quinazolinones |
| DK623586A (da) * | 1985-12-27 | 1987-06-28 | Eisai Co Ltd | Piperidinderivater eller salte deraf og farmaceutiske kompositioner indeholdende forbindelserne |
| US4874766A (en) * | 1986-09-22 | 1989-10-17 | Janssen Pharmaceutica N.V. | Method of promoting wound-healing |
| ES2094718T3 (es) * | 1986-09-22 | 1997-02-01 | Janssen Pharmaceutica Nv | Antagonistas de la serotonine para el tratamiento de heridas. |
| JP2660407B2 (ja) * | 1986-09-26 | 1997-10-08 | 住友製薬株式会社 | 新規なイミド誘導体 |
| JPH0434361Y2 (pl) * | 1986-12-25 | 1992-08-17 | ||
| DE3738844A1 (de) * | 1987-11-16 | 1989-05-24 | Merck Patent Gmbh | Analgetikum |
| EP0335442B1 (en) * | 1988-03-28 | 1996-05-15 | Janssen Pharmaceutica N.V. | Agents for preserving or restoring the soundness of the skin |
| IL90879A0 (en) * | 1988-09-02 | 1990-02-09 | Janssen Pharmaceutica Nv | 3-piperidinyl-indazole derivatives,their preparation and antihypertensive compositions containing them |
| CA1340821C (en) * | 1988-10-06 | 1999-11-16 | Nobuyuki Fukazawa | Heterocyclic compounds and anticancer-drug reinforcing agents containing them as effective components |
| FR2644786B1 (fr) * | 1989-03-21 | 1993-12-31 | Adir Cie | Nouveaux derives fluoro-4 benzoiques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| JP2744634B2 (ja) * | 1989-04-14 | 1998-04-28 | 三菱重工業株式会社 | ゴミ焼却装置 |
| US5776963A (en) * | 1989-05-19 | 1998-07-07 | Hoechst Marion Roussel, Inc. | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
| US5364866A (en) | 1989-05-19 | 1994-11-15 | Hoechst-Roussel Pharmaceuticals, Inc. | Heteroarylpiperidines, pyrrolidines and piperazines and their use as antipsychotics and analetics |
| US5561128A (en) * | 1989-05-19 | 1996-10-01 | Hoechst-Roussel Pharmaceuticals, Inc. | N-[(4-(heteroaryl)-1-piperidinyl)alkyl]-10,11-dihydro-5H-dibenz[B,F]azepines and related compounds and their therapeutic utility |
| IE913473A1 (en) * | 1990-10-15 | 1992-04-22 | Fujisawa Pharmaceutical Co | Quinazoline derivatives and their preparation |
| US5158953A (en) * | 1991-08-13 | 1992-10-27 | National Science Council | 2-substituted methyl-2,3-dihydroimidazo[1,2-c]quinazolin-5(6H)-ones (thiones), the preparation and use thereof |
| DE4138756A1 (de) * | 1991-11-26 | 1993-05-27 | Troponwerke Gmbh & Co Kg | Kombination mit neuroprotektiver wirkung |
| US5266571A (en) * | 1992-01-09 | 1993-11-30 | Amer Moh Samir | Treatment of hemorrhoids with 5-HT2 antagonists |
| GB9202915D0 (en) * | 1992-02-12 | 1992-03-25 | Wellcome Found | Chemical compounds |
| KR100269756B1 (ko) * | 1992-02-13 | 2000-10-16 | 슈테펜엘.네스비트 | 피페리디닐티아시클릭유도체(Piperidinyl Thiacyclic Derivatives) |
| FR2696744B1 (fr) * | 1992-10-12 | 1994-12-30 | Logeais Labor Jacques | Dérivés de 2-pyrrolidone, leur procédé de préparation et leurs applications en thérapeutique. |
| EP0626373B1 (en) * | 1993-05-26 | 1998-12-23 | Sumitomo Pharmaceuticals Company, Limited | Quinazolinone derivatives |
| JP3645906B2 (ja) * | 1993-11-19 | 2005-05-11 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | マイクロカプセル封入された３−ピペリジニル−置換１，２−ベンズイソオキサゾール類及び１，２−ベンズイソチアゾール類 |
| EP0661266A1 (en) * | 1993-12-27 | 1995-07-05 | Toa Eiyo Ltd. | Substituted cyclic amine compounds as 5HT2 antagonists |
| US6184377B1 (en) | 1997-12-15 | 2001-02-06 | Sepracor Inc. | Compositions containing N-amino- and N-hydroxy-quinazolinones and methods for preparing libraries thereof |
| EP1122253B1 (en) * | 1998-10-16 | 2005-08-17 | Sumitomo Pharmaceuticals Company, Limited | Quinazolinone derivatives |
| GB9903784D0 (en) * | 1999-02-18 | 1999-04-14 | Lilly Co Eli | Pharmaceutical compounds |
| KR20010108394A (ko) * | 1999-03-26 | 2001-12-07 | 다비드 에 질레스 | 신규 화합물 |
| US6476041B1 (en) * | 1999-10-29 | 2002-11-05 | Merck & Co., Inc. | 1,4 substituted piperidinyl NMDA/NR2B antagonists |
| US6844338B2 (en) | 2000-05-18 | 2005-01-18 | Eli Lilly And Company | Piperidyindoles as serotonin receptor ligands |
| GB2362381A (en) * | 2000-05-18 | 2001-11-21 | Lilly Co Eli | Pharmaceutically active indolyl-piperidines |
| GB0013060D0 (en) * | 2000-05-31 | 2000-07-19 | Astrazeneca Ab | Chemical compounds |
| GB0021670D0 (en) * | 2000-09-04 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| DE10101324C1 (de) * | 2001-01-13 | 2001-12-13 | Ibfb Gmbh Privates Inst Fuer B | 1-Dimercaptoalkylchinazolin-2,4-(1H,3H)-dione als Matrix-Metalloproteinase(MMP)-Inhibitoren |
| GB0117899D0 (en) * | 2001-07-23 | 2001-09-12 | Astrazeneca Ab | Chemical compounds |
| SE0102809D0 (sv) * | 2001-08-22 | 2001-08-22 | Astrazeneca Ab | Novel compounds |
| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
| TWI324597B (en) * | 2002-03-28 | 2010-05-11 | Astrazeneca Ab | Quinazoline derivatives |
| US6924285B2 (en) * | 2002-03-30 | 2005-08-02 | Boehringer Ingelheim Pharma Gmbh & Co. | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| EP1560814A1 (en) * | 2002-11-13 | 2005-08-10 | Synthon B.V. | Process for making risperidone and intermediates therefor |
| GB0309009D0 (en) * | 2003-04-22 | 2003-05-28 | Astrazeneca Ab | Quinazoline derivatives |
| EP1615923A1 (en) * | 2003-04-22 | 2006-01-18 | Synthon B.V. | Risperidone monohydrochloride |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| WO2005026151A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| AU2004272345A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| ATE395346T1 (de) * | 2003-09-16 | 2008-05-15 | Astrazeneca Ab | Chinazolinderivate als tyrosinkinaseinhibitoren |
| SI1667992T1 (sl) * | 2003-09-19 | 2007-06-30 | Astrazeneca Ab | Kinazolinski derivati |
| US20070037837A1 (en) * | 2003-09-19 | 2007-02-15 | Hennequin Laurent Francois A | Quinazoline derivatives |
| JP2007506716A (ja) * | 2003-09-25 | 2007-03-22 | アストラゼネカ アクチボラグ | キナゾリン誘導体 |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| MXPA06004304A (es) * | 2003-10-24 | 2006-06-05 | Hoffmann La Roche | Antagonistas del receptor ccr-3. |
| GB0326459D0 (en) * | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| KR101118582B1 (ko) | 2003-11-20 | 2012-02-27 | 얀센 파마슈티카 엔.브이. | 폴리(ａｄｐ-리보스)폴리머라제 저해제로서의 6-알케닐 및6-페닐알킬 치환된 2-퀴놀리논 및 2-퀴녹살리논 |
| NZ546990A (en) * | 2003-11-20 | 2010-03-26 | Janssen Pharmaceutica Nv | 7-Phenylalkyl substituted 2-quinolinones and 2 quinoxalinones as poly(adp-ribose) polymerase inhibitors |
| US7879857B2 (en) * | 2003-12-05 | 2011-02-01 | Janssen Pharmaceutica Nv | 6-substituted 2-quinolinones and 2-quinoxalinones as poly (adp-ribose) polymerase inhibitors |
| CN1914182B (zh) * | 2004-02-03 | 2011-09-07 | 阿斯利康(瑞典)有限公司 | 喹唑啉衍生物 |
| US20070232607A1 (en) * | 2004-06-04 | 2007-10-04 | Bradbury Robert H | Quinazoline Derivatives as Erbb Receptor Tyrosine kinases |
| NZ551680A (en) * | 2004-06-30 | 2010-02-26 | Janssen Pharmaceutica Nv | Quinazolinone derivatives as PARP inhibitors |
| MXPA06014541A (es) * | 2004-06-30 | 2007-03-23 | Janssen Pharmaceutica Nv | Derivados de quinazolindiona como inhibidores de la poli(adp-ribosa) polimerasa. |
| MXPA06014542A (es) * | 2004-06-30 | 2007-03-23 | Janssen Pharmaceutica Nv | Derivados de ftalazina como inhibidores de poli(adp-ribosa) polimerasa-i. |
| ATE501148T1 (de) | 2004-12-14 | 2011-03-15 | Astrazeneca Ab | Pyrazolopyrimidinverbindungen als antitumormittel |
| JP5054544B2 (ja) * | 2005-02-26 | 2012-10-24 | アストラゼネカ アクチボラグ | チロシンキナーゼ阻害剤としてのキナゾリン誘導体 |
| GB0504474D0 (en) * | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| GB0508717D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| GB0508715D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| DE602006018331D1 (de) * | 2005-09-20 | 2010-12-30 | Astrazeneca Ab | 4-(1h-indazol-5-ylamino)chinazolinverbindungen als inhibitoren der erbb-rezeptortyrosinkinase zur behandlung von krebs |
| EP1940825A1 (en) * | 2005-09-20 | 2008-07-09 | Astra Zeneca AB | Quinazoline derivatives as anticancer agents |
| JP2009517450A (ja) * | 2005-12-02 | 2009-04-30 | アストラゼネカ アクチボラグ | チロシンキナーゼ阻害薬としての４−アニリノ置換キナゾリン誘導体 |
| CN101321739A (zh) * | 2005-12-02 | 2008-12-10 | 阿斯利康(瑞典)有限公司 | 用作erbB酪氨酸激酶抑制剂的喹唑啉衍生物 |
| EP1921070A1 (de) * | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstelllung |
| WO2008095847A1 (de) * | 2007-02-06 | 2008-08-14 | Boehringer Ingelheim International Gmbh | Bicyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| WO2008107478A1 (en) * | 2007-03-08 | 2008-09-12 | Janssen Pharmaceutica Nv | Quinolinone derivatives as parp and tank inhibitors |
| US8404713B2 (en) * | 2007-10-26 | 2013-03-26 | Janssen Pharmaceutica Nv | Quinolinone derivatives as PARP inhibitors |
| EP2245026B1 (de) | 2008-02-07 | 2012-08-01 | Boehringer Ingelheim International GmbH | Spirocyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| RU2490260C2 (ru) | 2008-03-27 | 2013-08-20 | Янссен Фармацевтика Нв | Тетрагидрофенантридиноны и тетрагидроциклопентахинолиноны в качестве ингибиторов parp и ингибиторов полимеризации тубулина |
| ATE513818T1 (de) * | 2008-03-27 | 2011-07-15 | Janssen Pharmaceutica Nv | Chinazolinonderivate als tubulinpolymerisationshemmer |
| JP5739802B2 (ja) | 2008-05-13 | 2015-06-24 | アストラゼネカ アクチボラグ | ４−（３−クロロ−２−フルオロアニリノ）−７−メトキシ−６−｛［１−（ｎ−メチルカルバモイルメチル）ピペリジン−４−イル］オキシ｝キナゾリンのフマル酸塩 |
| EP2313397B1 (de) * | 2008-08-08 | 2016-04-20 | Boehringer Ingelheim International GmbH | Cyclohexyloxy-substituierte heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| CU24130B1 (es) | 2009-12-22 | 2015-09-29 | Novartis Ag | Isoquinolinonas y quinazolinonas sustituidas |
| US8440693B2 (en) | 2009-12-22 | 2013-05-14 | Novartis Ag | Substituted isoquinolinones and quinazolinones |
| BRPI1003506B1 (pt) | 2010-09-24 | 2019-12-03 | Ache Int Bvi Ltd | composto alquil-piperazino-fenil-4(3h)quinazolinonas e uso do composto alquil-piperazino-fenil-4(3h)quinazolinonas associado aos receptores serotoninérgicos 5-ht1a e 5-ht2a |
| CN104321325B (zh) | 2012-05-24 | 2016-11-16 | 诺华股份有限公司 | 吡咯并吡咯烷酮化合物 |
| EP2948451B1 (en) | 2013-01-22 | 2017-07-12 | Novartis AG | Substituted purinone compounds |
| WO2014115080A1 (en) | 2013-01-22 | 2014-07-31 | Novartis Ag | Pyrazolo[3,4-d]pyrimidinone compounds as inhibitors of the p53/mdm2 interaction |
| KR20160012194A (ko) | 2013-05-27 | 2016-02-02 | 노파르티스 아게 | 이미다조피롤리디논 유도체 및 질환의 치료에서의 그의 용도 |
| EP3004108B1 (en) | 2013-05-28 | 2017-10-18 | Novartis AG | Pyrazolo-pyrrolidin-4-one derivatives as bet inhibitors and their use in the treatment of disease |
| PL3004112T3 (pl) | 2013-05-28 | 2018-02-28 | Novartis Ag | Pochodne pirazolo-pirolidyn-4-onu oraz ich zastosowanie w leczeniu choroby |
| CN105916857B (zh) | 2013-11-21 | 2018-06-22 | 诺华股份有限公司 | 吡咯并吡咯酮衍生物及其作为bet抑制剂的用途 |
| EP3317278B1 (en) | 2015-07-01 | 2021-04-14 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| CN106866625B (zh) * | 2017-01-17 | 2019-12-13 | 上海鼎雅药物化学科技有限公司 | 酮色林的制备方法 |
| EP3658560A4 (en) | 2017-07-25 | 2021-01-06 | Crinetics Pharmaceuticals, Inc. | SOMATOSTAT IN MODULATORS AND USES THEREOF |
| CN109157507A (zh) * | 2018-09-14 | 2019-01-08 | 上海禾丰制药有限公司 | 酒石酸酮色林注射液及其制备方法 |
| CN112142760A (zh) * | 2020-10-20 | 2020-12-29 | 江苏法安德医药科技有限公司 | 一种酮色林中间体以及酮色林的制备方法 |
| WO2023133524A1 (en) * | 2022-01-06 | 2023-07-13 | Terran Biosciences, Inc. | A process for synthesizing ketanserin |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322766A (en) * | 1964-11-13 | 1967-05-30 | Shulton Inc | 3-beta-(4-pyridyl) ethyl-2, 3-dihydro-4(1h)-quinazolinones |
| US3635976A (en) * | 1967-12-20 | 1972-01-18 | Pennwalt Corp | 1 - heterocyclic alkyl-1 2 3 4-tetrahydroquinazolinones and analgesic intermediates thereof |
| US4096144A (en) * | 1970-12-08 | 1978-06-20 | Sumitomo Chemical Company, Limited | Process for preparing quinazolinone derivatives and their 2-(N-mono-substituted amino)-phenyl ketone intermediate derivatives |
| US4099002A (en) * | 1970-12-23 | 1978-07-04 | Sumitomo Chemical Company, Limited | Quinazolinone derivatives and a process for production thereof |
| US4146717A (en) * | 1972-04-07 | 1979-03-27 | Sumitomo Chemical Company, Limited | Nitroquinazolinone compounds having antiviral properties |
| US4035369A (en) * | 1975-10-08 | 1977-07-12 | Janssen Pharmaceutica N.V. | 1-Benzazolylalkyl-4-substituted-piperidines |
-
1979
- 1979-10-12 US US06/084,272 patent/US4335127A/en not_active Expired - Lifetime
- 1979-12-21 GR GR60828A patent/GR67304B/el unknown
-
1980
- 1980-01-04 MA MA18891A patent/MA18694A1/fr unknown
- 1980-01-07 LU LU88219C patent/LU88219I2/xx unknown
- 1980-01-07 CS CS80157A patent/CS223977B2/cs unknown
- 1980-01-07 PL PL1980221249A patent/PL125789B1/pl unknown
- 1980-01-07 SU SU802863403A patent/SU1041034A3/ru active
- 1980-01-07 PT PT70662A patent/PT70662A/pt unknown
- 1980-01-07 CY CY1252A patent/CY1252A/xx unknown
- 1980-01-07 NO NO800034A patent/NO155243C/no unknown
- 1980-01-07 DE DE8080300059T patent/DE3065489D1/de not_active Expired
- 1980-01-07 IE IE21/80A patent/IE49351B1/en not_active IP Right Cessation
- 1980-01-07 IL IL59084A patent/IL59084A/xx unknown
- 1980-01-07 ZA ZA00800082A patent/ZA8082B/xx unknown
- 1980-01-07 HU HU8025A patent/HU184222B/hu unknown
- 1980-01-07 AT AT80300059T patent/ATE5258T1/de not_active IP Right Cessation
- 1980-01-07 DK DK007280A patent/DK170669B1/da not_active IP Right Cessation
- 1980-01-07 NZ NZ192551A patent/NZ192551A/en unknown
- 1980-01-07 EP EP80300059A patent/EP0013612B1/en not_active Expired
- 1980-01-07 FI FI800047A patent/FI66609C/fi not_active IP Right Cessation
- 1980-01-07 AU AU54381/80A patent/AU536175B2/en not_active Expired
- 1980-01-07 JP JP18680A patent/JPS55105679A/ja active Granted
- 1980-01-07 CA CA343,181A patent/CA1132557A/en not_active Expired
- 1980-01-08 PH PH23489A patent/PH17114A/en unknown
- 1980-01-08 ES ES487537A patent/ES8101586A1/es not_active Expired
- 1980-01-08 YU YU46/80A patent/YU42957B/xx unknown
- 1980-01-21 KR KR1019800000201A patent/KR850000684B1/ko active
- 1980-02-20 RO RO80100248A patent/RO79148A/ro unknown
-
1984
- 1984-07-06 SG SG486/84A patent/SG48684G/en unknown
- 1984-08-02 KR KR1019840004608A patent/KR850000677B1/ko not_active IP Right Cessation
- 1984-10-11 HK HK762/84A patent/HK76284A/xx not_active IP Right Cessation
- 1984-12-20 KR KR1019840008162A patent/KR850000683B1/ko not_active IP Right Cessation
-
1987
- 1987-12-30 MY MY555/87A patent/MY8700555A/xx unknown
-
1993
- 1993-03-02 NL NL930018C patent/NL930018I2/nl unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL125789B1 (en) | Process for preparing novel derivatives of quinazoline | |
| DE60130562D1 (de) | Azaindolderivate, verfahren zu ihrer herstellung und ihre verwendung als antitumormittel | |
| IE61724B1 (en) | Aryl-subsituted (N-piperidinyl)methyl-and(N-piperazinyl)methylazoles having antipsychotic properties | |
| CA2148082A1 (en) | Imidazoquinazoline derivatives | |
| ES2001936A6 (es) | Procedimiento para la preparacion de indoles sustituidos con heterociclos. | |
| PT1178967E (pt) | Derivados de quinolina como inibidores de enzimas mek | |
| ATE229527T1 (de) | Pyrazolopyridylpyrazinon-derivate und ein verfahren zu ihrer herstellung | |
| ZA200704216B (en) | Phenylpiperazine derivatives with a combination of parti dopamine-D2 receptor agonism and serotonin reuptak inhibition | |
| PL139498B1 (en) | Process for preparing novel derivatives of 4-amino-6,7-dimethoxyquinoline | |
| KR870007180A (ko) | 티에노-1,4-디아제핀의 제조방법 | |
| DE69908546D1 (de) | Imidazopyridinderivate und Verfahren zu ihrer Herstellung | |
| IE810485L (en) | Imidazo compounds | |
| DE3772104D1 (de) | 4(5)-substituierte imidazol-derivate und zwischenverbindungen und verfahren zu ihrer herstellung. | |
| CA1257261A (en) | 4-alkoxy-pyrido[2,3-d]pyrimidine derivatives, process for their preparation and pharmaceutical compositions containing them | |
| TW358091B (en) | Method for preparing N-monosubstituted and N, N'-disubstituted unsymmetrical cyclic ureas | |
| DE69909848D1 (de) | Verfahren zur herstellung substituierter allylamin derivative und deren salze | |
| EP1214321B1 (en) | Process for production of naphthyridine-3-carboxylic acid derivatives | |
| AU773698B2 (en) | Intermediates for the production of quinolone carboxylic acid derivatives | |
| IL44163A (en) | Isoindoline derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same | |
| ZA200609447B (en) | Substituted cyclic urea derivatives | |
| IL131177A0 (en) | Process for the preparation of nicotinic acids | |
| HU902624D0 (en) | Process for the preparation of acryloyl-piperazine derivatives and pharmaceutical compositions containing them | |
| NZ200857A (en) | Preparation of 5,6,7,7a-tetrahydro-4h-thienol(3,2-e)pyridin-2-ones | |
| AU641513B2 (en) | 5-isothiazolamine derivatives | |
| Wentland et al. | Cyclic variations of 3-quinolinecarboxamides and effects on antiherpetic activity |