GB1019783A - Xanthenes and thioxanthenes - Google Patents
Xanthenes and thioxanthenesInfo
- Publication number
- GB1019783A GB1019783A GB34612/64A GB3461264A GB1019783A GB 1019783 A GB1019783 A GB 1019783A GB 34612/64 A GB34612/64 A GB 34612/64A GB 3461264 A GB3461264 A GB 3461264A GB 1019783 A GB1019783 A GB 1019783A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- compounds
- methyl
- choh
- piperidino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000005075 thioxanthenes Chemical class 0.000 title 1
- 150000003732 xanthenes Chemical class 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- -1 piperidino, hexamethyleneimino, pyrrolidino, morpholino, piperazino Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- MDTREROSCDWIHF-UHFFFAOYSA-N 1-chloro-4-methylxanthen-9-one Chemical compound O1C2=CC=CC=C2C(=O)C2=C1C(C)=CC=C2Cl MDTREROSCDWIHF-UHFFFAOYSA-N 0.000 abstract 1
- NIBFJPXGNVPNHK-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-4-carbaldehyde Chemical group C1=CC(C=O)=C2OC(F)(F)OC2=C1 NIBFJPXGNVPNHK-UHFFFAOYSA-N 0.000 abstract 1
- DBSDZVMWEMKFCH-UHFFFAOYSA-N 2-(2-methylpiperidin-1-yl)ethanamine Chemical compound CC1CCCCN1CCN DBSDZVMWEMKFCH-UHFFFAOYSA-N 0.000 abstract 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical class OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 abstract 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 150000007514 bases Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000001843 schistosomicidal effect Effects 0.000 abstract 1
- 150000007659 semicarbazones Chemical class 0.000 abstract 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 abstract 1
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
-
- 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:1019783/C2/1> wherein X is =CO, =CHOH, =CH2; Z is -O-, -S-, =SO, or =SO2; Q is H or 1-3 halogen atoms, C1-6-alkyl or -alkoxy groups in positions 5, 6, 7 and 8 of the tricyclic ring; R is -CH2OH (or an ester thereof including carbanilates and nitrobenzoates) or CHO (or a semicarbazone or a thiosemicarbazone thereof; Y is C2-4-alkylene having its terminal valencies on different C atoms; R3 is H or C1-6-alkyl; R1 is H or C1-6-alkyl C2-6-2-hydroxyalkyl; and R2 is C1-6-alkyl or C2-6-2-hydroxyalky or R1 and R2 together with N- is piperidino, hexamethyleneimino, pyrrolidino, morpholino, piperazino or a C1-6-alkyl derivative thereof or a 5,6,7,8-tetrahydro-derivative thereof; acid addition salts of the above bases, and their preparation by subjecting the corresponding 4-methyl compound to the fermentative enzymatic action of a micro-organism capable of effecting oxidation of the 4-methyl group to 4-hydroxymethyl and to 4-formyl, said organism being of the order of Moniliales, Mucorates or Sphaeriaeles and, if desired, forming the acid addition salt of a basic compound so obtained. Compounds where X is CHOH are prepared also by reduction of compounds where X is CO and where X is SO by oxidation of the thiaxanthene. 4 - Methyl - 1 - [2 - (2 - methylpiperidino)-ethylamino] xanthene-9-one is prepared from 1-chloro-4-methylxanthen-9-one and 2-(2-methyl-piperidino)ethylamine. Pharmaceutical compositions comprise the compounds of the invention and a pharmaceutical carrier. The compositions, which have schistosomicidal activity, are administered orally to animals.
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL126381D NL126381C (en) | 1963-09-09 | ||
| IL21982A IL21982A (en) | 1963-09-09 | 1964-08-26 | Xanthene and thioxanthene derivatives |
| CH1133864A CH441376A (en) | 1963-09-09 | 1964-08-31 | Process and preparation of xanthenes and thioxanthenes |
| FR986811A FR4071M (en) | 1963-09-09 | 1964-09-01 | |
| BE652609D BE652609A (en) | 1963-09-09 | 1964-09-02 | |
| BR162358/64A BR6462358D0 (en) | 1963-09-09 | 1964-09-03 | PROCESS TO PRODUCE SUBSTITUTED THIO-XANTHENS AND XANTHENS |
| NL6410359A NL6410359A (en) | 1963-09-09 | 1964-09-04 | |
| DE19641518352 DE1518352A1 (en) | 1963-09-09 | 1964-09-07 | Process for the production of xanthenes |
| DK442764AA DK116663B (en) | 1963-09-09 | 1964-09-08 | Process for the preparation of 4-hydroxymethyl- or 4-formyl-substituted xanthenes or thioxanthenes or acid addition salts thereof. |
| SE10805/64A SE313316B (en) | 1963-09-09 | 1964-09-09 | |
| US463908A US3294803A (en) | 1963-09-09 | 1965-06-14 | 1-aminoalkylamino-4-hydroxymethyl (or 4-formyl)-thioxanthene derivatives |
| MY164/69A MY6900164A (en) | 1963-09-09 | 1969-12-30 | Xanthenes and thioxanthenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30737463A | 1963-09-09 | 1963-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1019783A true GB1019783A (en) | 1966-02-09 |
Family
ID=23189477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34612/64A Expired GB1019783A (en) | 1963-09-09 | 1964-08-24 | Xanthenes and thioxanthenes |
Country Status (3)
| Country | Link |
|---|---|
| AT (1) | AT270899B (en) |
| ES (1) | ES303758A1 (en) |
| GB (1) | GB1019783A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2282890A1 (en) * | 1974-08-30 | 1976-03-26 | Parke Davis & Co | 6-Chloro-4-methyl-1-(4-methyl-1-piperazinyl)thio-xanthen-9-ones - their 4-hydro xymethyl derivs and N-oxides, schistosomicides |
-
1964
- 1964-08-24 GB GB34612/64A patent/GB1019783A/en not_active Expired
- 1964-09-04 ES ES0303758A patent/ES303758A1/en not_active Expired
- 1964-09-08 AT AT773364A patent/AT270899B/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2282890A1 (en) * | 1974-08-30 | 1976-03-26 | Parke Davis & Co | 6-Chloro-4-methyl-1-(4-methyl-1-piperazinyl)thio-xanthen-9-ones - their 4-hydro xymethyl derivs and N-oxides, schistosomicides |
Also Published As
| Publication number | Publication date |
|---|---|
| AT270899B (en) | 1969-05-12 |
| ES303758A1 (en) | 1965-02-01 |
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