NO149964B - Analogifremgangsmaate ved fremstilling av terapeutisk aktive 3-(tetrazol-5-yl)-1-azaxanthoner - Google Patents
Analogifremgangsmaate ved fremstilling av terapeutisk aktive 3-(tetrazol-5-yl)-1-azaxanthoner Download PDFInfo
- Publication number
- NO149964B NO149964B NO783233A NO783233A NO149964B NO 149964 B NO149964 B NO 149964B NO 783233 A NO783233 A NO 783233A NO 783233 A NO783233 A NO 783233A NO 149964 B NO149964 B NO 149964B
- Authority
- NO
- Norway
- Prior art keywords
- preparation
- azaxanthones
- tetrazol
- pyridyl
- therapeutic active
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 TETRAZOL-5-YL Chemical class 0.000 title description 2
- 230000001225 therapeutic effect Effects 0.000 title description 2
- MMXYNKLYVRNTCK-UHFFFAOYSA-N diphenyl-2-pyridylmethane Chemical class C1=CC=CC=C1C(C=1N=CC=CC=1)C1=CC=CC=C1 MMXYNKLYVRNTCK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 229940125722 laxative agent Drugs 0.000 description 1
- UMWMJMJPVRELFU-UHFFFAOYSA-N nitrosulfamic acid Chemical compound OS(=O)(=O)N[N+]([O-])=O UMWMJMJPVRELFU-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PGOJBUZQXOJVGW-UHFFFAOYSA-N phenyl(pyridin-2-yl)methanediol Chemical compound OC(O)(C1=NC=CC=C1)C1=CC=CC=C1 PGOJBUZQXOJVGW-UHFFFAOYSA-N 0.000 description 1
- UYESUYBXKHPUDU-UHFFFAOYSA-N phenyl(pyridin-2-yl)methanol Chemical compound C=1C=CC=NC=1C(O)C1=CC=CC=C1 UYESUYBXKHPUDU-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Color Printing (AREA)
Description
Fremgangsmåte til fremstilling av difenyl-pyridyl-metanforbindelser.
Nærværende oppfinnelse angår en hittil ukjent fremgangsmåte til fremstilling av difenyl-pyridyl-metanforbindelser med den generelle formel:
hvor X betegner et hydrogen- eller halogenatom eller en alkyl-, hydroksy-, alkoksy-, aryl-, aralkyl-, nitro-, amino-, sulfonsyre eller acyloksygruppe og Z betegner et hydrogenatom eller en alkylgruppe eller et halogenatom.
Disse stoffer har i de senere år funnet utstrakt terapeutisk anvendelse i særdeleshet som desinfeksjonsmidler og som laxantia.
En kjent fremgangsmåte til fremstilling av stoffer av denne art går ut fra pyridinaldehyd eller pyridinketon eventuelt substituert i pyridinringen, idet disse stoffer kondenseres med fenoler i nærvær av vannbindende midler.
Denne fremgangsmåte lider imidlertid av den ulempe at det ved denne bare vil kunne fremstilles forbindelser, hvor* de to fe-nylgrupper enten er usubstituert eller likt substituert, mens det er umulig på denne måte å oppnå en usymmetrisk substitusjon i disse grupper.
,Det kjennes også en fremgangsmåte til fremstilling av de samme forbindelser hvor en hydroksy-fenyl-pyridylkarbinol eller et O-alkyl- eller O-acyl-derivat av denne omsettes med et fenol som er usubstituert i p-stilling til hydroksygruppen, i nærvær av sure, vannfraspaltende midler. Denne fremgangsmåte tillater fremstilling av asymmetrisk substituerte produkter.
Det har nå overraskende vist seg at de angjeldende di-fenyl-pyridyl-metanforbindelser på særlig enkel og teknisk lett gjen-nomførbar måte kan fremstilles ved at en fenylpyridylmetanol med den generelle formel:
hvor X og Z har samme betydning som foran angitt,
i surt miljo kondenseres med anilin, hvoretter kondensasjons-produktet diazoteres og omkokes uten isolering av mellompro-duktet.
Det er overraskende at omsetningen mellom karbinol og anilin i surt miljo forloper glatt i anilinets para-stilling i forhold til aminogruppen. Ved således i stedet for fenol til konden-sas jonsprosessen å anvende den foran anforte fremgangsmåte oppnås som det har vist seg ved undersokelser såvel i labora-torium som i teknisk målestokk, en vesentlig forenkling av den tidligere kjente, idet det samtidig, slik som det vil fremgå av nedenstående eksempel, oppnås et godt utbytte ved denne fremgangsmåte.
Til frembringelse av det sure miljo vil kunne anvendes de van-lige til kondensasjonsreaksjonen vannbindende midler som svo-
/ velsyre, konsentrert saltsyre, sinkklorid, fosforsyre, stanni-klorid og lignende forbindelser.
Oppfinnelsen vil i det folgende bli nærmere forklart ved eksempel.
EKSEMPEL
Fremstilling av 4, 41- dihydroksv- difenyl- pyridyl- 2- metan.
6,45 g p-metoksy-fenyl-pyridyl-2-metanol, 2,8 g anilin og 25 ml 50 % svovelsyre kokes under tilbakelopskjoling i 8 timer. Når
blandingen er avkjolt litt, tilsettes 9 ml 60 % bromhydrogen-syre, og kokingen fortsettes i 5 timer. Etter avkjoling fjer-nes kjoleren, og reaksjonskolben anbringes i et isbad. Under
omroring tilsettes heretter fra en skilletrakt i lopet av ca.
5 minutter en opplosning av 2,2 g natriumnitritt i 10 ml vann. Reaksjonsblandingen helles heretter forsiktig over i 25 ml kokende 25 % svovelsyre, og blandingen holdes kokende i 1/2 time. Blandingen avkjoles, hvorved det utskilles et brunlig bunnfall, og væsken filtreres fra. Av den sure væsken utfelles 4,4'-dihydroksy-difenyl-pyridyl-2-metan ved hjelp av lo % natriumhydroksyd som et gulaktig pulver. Av det brunlige bunnfall kan oppnås mer 4,4'-dihydroksy-difenyl-pyridyl-2-metan. Bunnfallet opploses i base, hvoretter opplosningen gjores sur. Etter filtrering felles med 10 % natriumhydroksyd som ovenfor.
Det oppnådde 4,4'-dihydroksy-difenyl-pyridyl-2-metan har smeltepunkt 210 - 215° (spaltning), og diacetylderivatet har smeltepunkt 134 - 135 . Utbytte: 4,55 g, svarende til 55 % av det teoretiske utbytte.
Claims (1)
- Fremgangsmåte til fremstilling av difenyl-pyridyl-metanforbindelser med den generelle formel:hvor X betegner et hydrogen- eller halogenatom eller an alkyl-, hydroksy-, alkoksy-, aryl-, aralkyl-,
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52115817A JPS5825677B2 (ja) | 1977-09-26 | 1977-09-26 | ３−テトラゾ−ル−１−アザキサントン誘導体およびその製造法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO783233L NO783233L (no) | 1979-03-27 |
| NO149964B true NO149964B (no) | 1984-04-16 |
| NO149964C NO149964C (no) | 1984-07-25 |
Family
ID=14671828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO783233A NO149964C (no) | 1977-09-26 | 1978-09-25 | Analogifremgangsmaate ved fremstilling av terapeutisk aktive 3-(tetrazol-5-yl)-1-azaxanthoner |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4267332A (no) |
| JP (1) | JPS5825677B2 (no) |
| AT (1) | AT360988B (no) |
| AU (1) | AU522242B2 (no) |
| BE (1) | BE870736A (no) |
| CA (1) | CA1090344A (no) |
| CH (1) | CH638525A5 (no) |
| DE (1) | DE2841644A1 (no) |
| DK (1) | DK156725C (no) |
| ES (1) | ES473680A1 (no) |
| FR (1) | FR2404011A1 (no) |
| GB (1) | GB2004551B (no) |
| GR (1) | GR64802B (no) |
| HU (1) | HU178360B (no) |
| IT (1) | IT1101604B (no) |
| NL (1) | NL188579C (no) |
| NO (1) | NO149964C (no) |
| SE (1) | SE434748B (no) |
| SU (1) | SU858570A3 (no) |
| ZA (1) | ZA785054B (no) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61172880A (ja) * | 1985-01-28 | 1986-08-04 | Takeda Chem Ind Ltd | ２−アミノ−５−オキソ−５Ｈ−〔１〕ベンゾピラノ〔２，３−ｂ〕ピリジン−３−カルボン酸誘導体およびその製造法 |
| JPS61215393A (ja) * | 1985-03-20 | 1986-09-25 | Takeda Chem Ind Ltd | ２−アミノ−５−オキソ−５Ｈ−〔１〕ベンゾピラノ〔２，３−ｂ〕ピリジン−３−カルボン酸誘導体およびその製造法 |
| US5831117A (en) | 1995-01-20 | 1998-11-03 | G. D. Searle & Co. | Method of preparing retroviral protease inhibitor intermediates |
| JPH08325248A (ja) * | 1995-05-26 | 1996-12-10 | Chugoku Kayaku Kk | テトラゾール類の新規な合成試薬及びそれを用いたテトラゾール類の製造方法 |
| KR980008226A (ko) * | 1996-07-05 | 1998-04-30 | 다케다 쿠니오 | 시각기능장애의 예방 및 치료제 |
| US7268454B2 (en) * | 2003-01-17 | 2007-09-11 | Magnetic Torque International, Ltd. | Power generating systems |
| US10214536B2 (en) | 2016-01-29 | 2019-02-26 | The Regents Of The University Of Michigan | Amlexanox analogs |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1403487A (en) * | 1972-07-21 | 1975-08-28 | Yoshitomi Pharmaceutical | Heterocyclic substituted alkanoic acids and derivatives |
| NL7403583A (no) * | 1973-03-19 | 1974-09-23 | ||
| JPS576433B2 (no) * | 1973-06-26 | 1982-02-04 | ||
| JPS5516432B2 (no) * | 1974-05-28 | 1980-05-01 |
-
1977
- 1977-09-26 JP JP52115817A patent/JPS5825677B2/ja not_active Expired
-
1978
- 1978-09-01 AU AU39488/78A patent/AU522242B2/en not_active Expired
- 1978-09-01 GR GR57139A patent/GR64802B/el unknown
- 1978-09-06 ZA ZA00785054A patent/ZA785054B/xx unknown
- 1978-09-18 US US06/942,925 patent/US4267332A/en not_active Expired - Lifetime
- 1978-09-19 GB GB7837321A patent/GB2004551B/en not_active Expired
- 1978-09-19 SE SE7809833A patent/SE434748B/sv not_active IP Right Cessation
- 1978-09-21 DK DK418678A patent/DK156725C/da not_active IP Right Cessation
- 1978-09-22 AT AT685478A patent/AT360988B/de not_active IP Right Cessation
- 1978-09-22 CA CA311,947A patent/CA1090344A/en not_active Expired
- 1978-09-22 HU HU78TA1495A patent/HU178360B/hu not_active IP Right Cessation
- 1978-09-22 IT IT27984/78A patent/IT1101604B/it active
- 1978-09-25 DE DE19782841644 patent/DE2841644A1/de active Granted
- 1978-09-25 SU SU782668856A patent/SU858570A3/ru active
- 1978-09-25 BE BE190684A patent/BE870736A/xx not_active IP Right Cessation
- 1978-09-25 FR FR7827423A patent/FR2404011A1/fr active Granted
- 1978-09-25 NO NO783233A patent/NO149964C/no unknown
- 1978-09-26 ES ES473680A patent/ES473680A1/es not_active Expired
- 1978-09-26 CH CH1003678A patent/CH638525A5/de not_active IP Right Cessation
- 1978-09-26 NL NLAANVRAGE7809741,A patent/NL188579C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1090344A (en) | 1980-11-25 |
| FR2404011A1 (fr) | 1979-04-20 |
| BE870736A (fr) | 1979-03-26 |
| SE7809833L (sv) | 1979-03-27 |
| JPS5825677B2 (ja) | 1983-05-28 |
| CH638525A5 (de) | 1983-09-30 |
| SE434748B (sv) | 1984-08-13 |
| NL7809741A (nl) | 1979-03-28 |
| US4267332A (en) | 1981-05-12 |
| AT360988B (de) | 1981-02-10 |
| DE2841644A1 (de) | 1979-04-05 |
| SU858570A3 (ru) | 1981-08-23 |
| AU522242B2 (en) | 1982-05-27 |
| DK418678A (da) | 1979-03-27 |
| HU178360B (en) | 1982-04-28 |
| IT1101604B (it) | 1985-10-07 |
| ES473680A1 (es) | 1979-04-16 |
| DK156725C (da) | 1990-03-05 |
| IT7827984A0 (it) | 1978-09-22 |
| ZA785054B (en) | 1979-08-29 |
| ATA685478A (de) | 1980-07-15 |
| FR2404011B1 (no) | 1981-08-14 |
| GB2004551B (en) | 1982-03-10 |
| NO783233L (no) | 1979-03-27 |
| AU3948878A (en) | 1980-03-06 |
| JPS5448798A (en) | 1979-04-17 |
| NL188579B (nl) | 1992-03-02 |
| DK156725B (da) | 1989-09-25 |
| GB2004551A (en) | 1979-04-04 |
| NO149964C (no) | 1984-07-25 |
| GR64802B (en) | 1980-06-02 |
| DE2841644C2 (no) | 1989-09-21 |
| NL188579C (nl) | 1992-08-03 |
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