FI69844C - Foerfarande foer framstaellning av etyl-4-(4-(1,5-dihydro-7-metyl-5-oxo(1,2,4)-triazolo(5,1-b)kinazolin-1-yl)alkyl)piperazin-1-karboxylater och saosom i foerfarandet mellanprodukter anvaendbara etyl-4-(4-(3-amino-6-metylkinazolin-2-ylamino)-alkyl)piperazin-1-karboxylater - Google Patents
Foerfarande foer framstaellning av etyl-4-(4-(1,5-dihydro-7-metyl-5-oxo(1,2,4)-triazolo(5,1-b)kinazolin-1-yl)alkyl)piperazin-1-karboxylater och saosom i foerfarandet mellanprodukter anvaendbara etyl-4-(4-(3-amino-6-metylkinazolin-2-ylamino)-alkyl)piperazin-1-karboxylater Download PDFInfo
- Publication number
- FI69844C FI69844C FI813478A FI813478A FI69844C FI 69844 C FI69844 C FI 69844C FI 813478 A FI813478 A FI 813478A FI 813478 A FI813478 A FI 813478A FI 69844 C FI69844 C FI 69844C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- alkyl
- piperazine
- compound
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- -1 3-AMINO-6-METHYLQUINAZOLIN-2-YLAMINO Chemical class 0.000 title claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title 2
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical class OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 claims description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N anhydrous methyl formate Natural products COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 230000022244 formylation Effects 0.000 claims description 2
- 238000006170 formylation reaction Methods 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical group COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-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
- 238000006722 reduction reaction Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 3
- QSTBSOVIUYYVQJ-UHFFFAOYSA-N ethyl 4-(4-aminobutyl)piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCN(CCCCN)CC1 QSTBSOVIUYYVQJ-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- AAVCEGPUGMZGHD-UHFFFAOYSA-N ethyl 4-(3-cyanopropyl)piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCN(CCCC#N)CC1 AAVCEGPUGMZGHD-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WOOIBJWFHSHPJN-UHFFFAOYSA-N 2h-triazolo[4,5-h]quinazoline Chemical compound C1=CC2=NNN=C2C2=NC=NC=C21 WOOIBJWFHSHPJN-UHFFFAOYSA-N 0.000 description 1
- ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 4-chlorobutanenitrile Chemical compound ClCCCC#N ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 0.000 description 1
- DSMFKIQLIKUWSX-UHFFFAOYSA-N C1CN(CCN1CCCC#N)C(=O)O Chemical compound C1CN(CCN1CCCC#N)C(=O)O DSMFKIQLIKUWSX-UHFFFAOYSA-N 0.000 description 1
- ISDOJTKDOLXMAH-UHFFFAOYSA-N CCN1CC(C(O)=O)N(CCCCNC(C)=O)CC1 Chemical compound CCN1CC(C(O)=O)N(CCCCNC(C)=O)CC1 ISDOJTKDOLXMAH-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000000172 allergic effect Effects 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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000000572 bronchospasmolytic effect Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- ROOFTMZYCCQKDC-UHFFFAOYSA-N ethyl 4-(4-acetamidobutyl)piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCN(CCCCNC(C)=O)CC1 ROOFTMZYCCQKDC-UHFFFAOYSA-N 0.000 description 1
- OMFDZIHIXYKKCC-UHFFFAOYSA-N ethyl 4-[4-[(3-amino-6-methyl-2h-quinazolin-2-yl)amino]butyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CCCCNC1N(N)C=C2C=C(C)C=CC2=N1 OMFDZIHIXYKKCC-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
- 150000004687 hexahydrates Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 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 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (5)
1. Förfarande för framställning av etyl~4-<4-(1,5-dihydro-7-metyl-5-oxo/l, 2,4_7triazolo/5, l-b/kinazolin- A 5 1-yl)alkyl -piperazin-l-karboxylater med formeln (I) / \ (CH~) -N N-COOR ! \ _J .. N N
10 A. 1 — ——N (I) CH3 0 15 väri n är ett heltal 2, 3, 4 eller 5 och R är lägre alkyl och deras syraadditionssalter med oorganiska eller orga-nista syror, kännetecknat därav, att en före-ning med formeln II 20 ^ N. NH-NH- 25 /L ^ N (II) ch3-^A^ -γ' nh2 o orasätts med en förening med formeln III 30 / v NH~-(CH0) -N N-COOR (III) 2. n \_/ 35 väri R och n har ovan angiven betydelse for erhällande av en förening med formeln IV 12 69844 (CH2 ] n_N\^ 'n-COOR jx I I <iv> 5 ''NHj 0 väri n och R har ovan angiven betydelse, och att fore- 10 ningen med formeln (IV) omsätts med ett formyleingsmedel, och att, om sa onskas föreningen med formeln I omvandlas till syraadditionssalt.
2. Förfarande enligt patentkravet 1, kanne-t e c k n a t darav, att 15 a) reaktionen mellan föreningen med formeln (II) och föreningen med formeln (III) utförs vid en temperatur av cirka 180°C, b) formyleringsmedlet utgörs av ett alkylorto-formiat, isynnerhet metyl- eller etylortoformiat och att 20 reaktionen utförs i dimetylformamid eller i myrsyra eller i dimetyl- eller dietylacetal av dimetylformamid eller i dimetylformamid i närvaro av en syraklorid, sasom bensoyl-klorid, c) formyleringen utförs i närvaro av ett surt medel, 25 sasom t.ex. paratoluensulfonsyra, i nägot inert lösnings- medel, sasom i toluen under äterflöde.
3. Etyl-4-/4-3-amino-6-metyIkinäzolin-2-y1amino) -alkyJ^piperazin-l-karboxylater, vilka är användbara säsom mellanprodukter vid framställning av föreningar med for- 30 mein I, kännetecknade därav, att de har formeln (IV)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8036025 | 1980-11-10 | ||
| GB8036025 | 1980-11-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI813478L FI813478L (fi) | 1982-05-11 |
| FI69844B FI69844B (fi) | 1985-12-31 |
| FI69844C true FI69844C (fi) | 1986-05-26 |
Family
ID=10517193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI813478A FI69844C (fi) | 1980-11-10 | 1981-11-04 | Foerfarande foer framstaellning av etyl-4-(4-(1,5-dihydro-7-metyl-5-oxo(1,2,4)-triazolo(5,1-b)kinazolin-1-yl)alkyl)piperazin-1-karboxylater och saosom i foerfarandet mellanprodukter anvaendbara etyl-4-(4-(3-amino-6-metylkinazolin-2-ylamino)-alkyl)piperazin-1-karboxylater |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4390697A (sv) |
| KR (1) | KR880001635B1 (sv) |
| DE (1) | DE3144650A1 (sv) |
| DK (1) | DK155939C (sv) |
| ES (1) | ES8303414A1 (sv) |
| FI (1) | FI69844C (sv) |
| FR (1) | FR2493850A1 (sv) |
| HU (1) | HU183723B (sv) |
| IL (1) | IL64012A (sv) |
| PT (1) | PT73953B (sv) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7893071B2 (en) * | 2001-04-23 | 2011-02-22 | University Of Virginia Patent Foundation | Synthesis and evaluation of novel phthalimide mimics as anti-angiogenic |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3053844A (en) * | 1959-04-13 | 1962-09-11 | Ici Ltd | Mono-acyl derivatives of s-triazolo [2, 3-c] pyrimidines |
| ZA81708B (en) * | 1980-02-14 | 1982-06-30 | Roussel Uclaf | Triazoloquinazolinone derivatives |
-
1981
- 1981-10-07 IL IL64012A patent/IL64012A/xx unknown
- 1981-10-26 KR KR1019810004059A patent/KR880001635B1/ko not_active Expired
- 1981-10-27 FR FR8120136A patent/FR2493850A1/fr active Granted
- 1981-11-03 US US06/317,858 patent/US4390697A/en not_active Expired - Fee Related
- 1981-11-04 FI FI813478A patent/FI69844C/fi not_active IP Right Cessation
- 1981-11-05 ES ES506858A patent/ES8303414A1/es not_active Expired
- 1981-11-09 HU HU813341A patent/HU183723B/hu not_active IP Right Cessation
- 1981-11-09 DK DK493681A patent/DK155939C/da not_active IP Right Cessation
- 1981-11-09 PT PT73953A patent/PT73953B/pt unknown
- 1981-11-10 DE DE19813144650 patent/DE3144650A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| IL64012A0 (en) | 1982-01-31 |
| PT73953A (fr) | 1981-12-01 |
| PT73953B (fr) | 1983-11-30 |
| DK493681A (da) | 1982-05-11 |
| DK155939B (da) | 1989-06-05 |
| ES506858A0 (es) | 1983-02-01 |
| KR830007652A (ko) | 1983-11-04 |
| IL64012A (en) | 1986-09-30 |
| DE3144650A1 (de) | 1982-08-26 |
| KR880001635B1 (ko) | 1988-09-03 |
| DK155939C (da) | 1989-10-23 |
| ES8303414A1 (es) | 1983-02-01 |
| FR2493850A1 (fr) | 1982-05-14 |
| FI69844B (fi) | 1985-12-31 |
| HU183723B (en) | 1984-05-28 |
| FR2493850B1 (sv) | 1984-03-16 |
| FI813478L (fi) | 1982-05-11 |
| US4390697A (en) | 1983-06-28 |
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