CA1145349A - Terminal bifunktional xylite-derivatives - Google Patents

Terminal bifunktional xylite-derivatives

Info

Publication number: CA1145349A
Authority: CA; Canada
Prior art keywords: xylitol; dianhydro; process according; formula; compound
Prior art date: 1978-05-11
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

Application number

CA000327317A

Other languages

English (en)

French (fr)

Inventor

Ildiko Nee Sandor Vidra

Laszlo Institoris

Sandor Eckhardt

Karoly Lapis

Andras Jeney

Laszlo Kopper

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chinoin Private Co Ltd

Original Assignee

Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

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.)

1978-05-11

Filing date

1979-05-10

Publication date

1983-04-26

1979-05-10 Application filed by Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

1983-04-26 Application granted granted Critical

1983-04-26 Publication of CA1145349A publication Critical patent/CA1145349A/en

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 33
229910052736 halogen Inorganic materials 0.000 claims abstract description 11
150000002367 halogens Chemical class 0.000 claims abstract description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
239000001301 oxygen Substances 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
239000000811 xylitol Substances 0.000 claims description 41
229960002675 xylitol Drugs 0.000 claims description 41
239000000243 solution Substances 0.000 claims description 30
238000000034 method Methods 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 19
239000011230 binding agent Substances 0.000 claims description 16
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 12
-1 3-benzoyl-1,5-dibromo-1,5-didesoxy-xylitol Chemical compound 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 9
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 8
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 8
235000010447 xylitol Nutrition 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 6
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
150000002431 hydrogen Chemical group 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
GSWQIGIUMPTMRX-VQFNDLOPSA-N C1(=CC=CC=C1)C1=CC=C(C(=O)[C@]([C@H](CBr)O)(O)[C@H](O)CBr)C=C1 Chemical compound C1(=CC=CC=C1)C1=CC=C(C(=O)[C@]([C@H](CBr)O)(O)[C@H](O)CBr)C=C1 GSWQIGIUMPTMRX-VQFNDLOPSA-N 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
239000012346 acetyl chloride Substances 0.000 claims description 2
150000001450 anions Chemical group 0.000 claims description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
239000000126 substance Substances 0.000 claims 6
238000004519 manufacturing process Methods 0.000 claims 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
239000003456 ion exchange resin Substances 0.000 claims 1
229920003303 ion-exchange polymer Polymers 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
230000001085 cytostatic effect Effects 0.000 abstract description 6
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 abstract description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
125000003435 aroyl group Chemical group 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
241001465754 Metazoa Species 0.000 description 14
239000004480 active ingredient Substances 0.000 description 11
239000008194 pharmaceutical composition Substances 0.000 description 10
238000002054 transplantation Methods 0.000 description 9
239000003826 tablet Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
241000699670 Mus sp. Species 0.000 description 6
206010028980 Neoplasm Diseases 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000012153 distilled water Substances 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
YGJKHTNKXAUYCR-SCDXWVJYSA-N BrC[C@H](O)[C@@H](O)[C@H](O)CBr Chemical compound BrC[C@H](O)[C@@H](O)[C@H](O)CBr YGJKHTNKXAUYCR-SCDXWVJYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
239000000654 additive Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000012043 crude product Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
FZQZRBQKXXGAMZ-UHFFFAOYSA-N 2-benzyl-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1CC1=CC=CC=C1 FZQZRBQKXXGAMZ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
206010003445 Ascites Diseases 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000003708 ampul Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
238000001802 infusion Methods 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
DHKVCYCWBUNNQH-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-6-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)C=NN2 DHKVCYCWBUNNQH-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
ZILGFHCSKFFZAT-SCDXWVJYSA-N ClC[C@H](O)[C@@H](O)[C@H](O)CCl Chemical compound ClC[C@H](O)[C@@H](O)[C@H](O)CCl ZILGFHCSKFFZAT-SCDXWVJYSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
QYEVBJRIMBKJCW-SCDXWVJYSA-N IC[C@H](O)[C@@H](O)[C@H](O)CI Chemical compound IC[C@H](O)[C@@H](O)[C@H](O)CI QYEVBJRIMBKJCW-SCDXWVJYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
241000700159 Rattus Species 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
125000004036 acetal group Chemical group 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000005325 alkali earth metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229960004977 anhydrous lactose Drugs 0.000 description 1
239000002585 base Substances 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
239000000824 cytostatic agent Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000010690 paraffinic oil Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
150000005846 sugar alcohols Chemical class 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/64—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/42—Polyhydroxylic acyclic alcohols
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Epoxy Compounds (AREA)
Saccharide Compounds (AREA)

CA000327317A 1978-05-11 1979-05-10 Terminal bifunktional xylite-derivatives Expired CA1145349A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU78CI1826A HU176216B (en)	1978-05-11	1978-05-11	Process for producing terminally bifuntional xylite derivatives of citostatic activity
HUCI-1826		1978-05-11

Publications (1)

Publication Number	Publication Date
CA1145349A true CA1145349A (en)	1983-04-26

Family

ID=10994695

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000327317A Expired CA1145349A (en)	1978-05-11	1979-05-10	Terminal bifunktional xylite-derivatives

Country Status (26)

Country	Link
JP (1)	JPS5522662A (cs)
AR (1)	AR222332A1 (cs)
AT (1)	AT361945B (cs)
BE (1)	BE876166A (cs)
CA (1)	CA1145349A (cs)
CH (1)	CH641437A5 (cs)
CS (1)	CS211399B2 (cs)
DD (1)	DD143765A5 (cs)
DE (1)	DE2917538A1 (cs)
DK (1)	DK195279A (cs)
EG (1)	EG15150A (cs)
ES (1)	ES480869A1 (cs)
FI (1)	FI67845C (cs)
FR (1)	FR2425445A1 (cs)
GB (1)	GB2024204B (cs)
GR (1)	GR68495B (cs)
HU (1)	HU176216B (cs)
IL (1)	IL57182A (cs)
IN (1)	IN150040B (cs)
IT (1)	IT1118485B (cs)
NL (1)	NL7903634A (cs)
NO (1)	NO153928C (cs)
PL (1)	PL121560B1 (cs)
SE (1)	SE7904080L (cs)
SU (1)	SU984410A3 (cs)
YU (1)	YU108079A (cs)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH381666A (de) *	1958-04-24	1964-09-15	Nat Res Dev	Verfahren zur Herstellung von Derivaten von polyhydrischen Alkoholen
DE1668241A1 (de) *	1968-03-06	1971-02-11	Herbrand Kg Dr	Therapeutisch wirksame 1,5-di-substituierte Derivate von Xylit,Adonit und Arabit

1978
- 1978-05-11 HU HU78CI1826A patent/HU176216B/hu unknown
1979
- 1979-04-30 DE DE19792917538 patent/DE2917538A1/de not_active Withdrawn
- 1979-04-30 IL IL57182A patent/IL57182A/xx unknown
- 1979-05-02 IN IN447/CAL/79A patent/IN150040B/en unknown
- 1979-05-06 EG EG264/79A patent/EG15150A/xx active
- 1979-05-07 GR GR59037A patent/GR68495B/el unknown
- 1979-05-09 FI FI791484A patent/FI67845C/fi not_active IP Right Cessation
- 1979-05-09 NL NL7903634A patent/NL7903634A/xx not_active Application Discontinuation
- 1979-05-09 SE SE7904080A patent/SE7904080L/xx not_active Application Discontinuation
- 1979-05-09 YU YU01080/79A patent/YU108079A/xx unknown
- 1979-05-09 FR FR7911733A patent/FR2425445A1/fr active Granted
- 1979-05-10 CS CS793205A patent/CS211399B2/cs unknown
- 1979-05-10 AR AR276464A patent/AR222332A1/es active
- 1979-05-10 IT IT67984/79A patent/IT1118485B/it active
- 1979-05-10 AT AT347779A patent/AT361945B/de not_active IP Right Cessation
- 1979-05-10 BE BE0/195089A patent/BE876166A/xx not_active IP Right Cessation
- 1979-05-10 CA CA000327317A patent/CA1145349A/en not_active Expired
- 1979-05-10 PL PL1979215489A patent/PL121560B1/pl unknown
- 1979-05-10 DK DK195279A patent/DK195279A/da not_active Application Discontinuation
- 1979-05-10 CH CH438979A patent/CH641437A5/de not_active IP Right Cessation
- 1979-05-10 JP JP5758879A patent/JPS5522662A/ja active Pending
- 1979-05-10 GB GB7916274A patent/GB2024204B/en not_active Expired
- 1979-05-10 NO NO791564A patent/NO153928C/no unknown
- 1979-05-11 ES ES480869A patent/ES480869A1/es not_active Expired
- 1979-05-11 DD DD79212780A patent/DD143765A5/de unknown
- 1979-05-11 SU SU792764801A patent/SU984410A3/ru active

Also Published As

Publication number	Publication date
NO153928C (no)	1986-06-18
GB2024204B (en)	1982-10-27
BE876166A (fr)	1979-09-03
HU176216B (en)	1981-01-28
FI791484A7 (fi)	1979-11-12
IL57182A0 (en)	1979-07-25
PL215489A1 (cs)	1980-02-11
NO153928B (no)	1986-03-10
ATA347779A (de)	1980-09-15
IN150040B (cs)	1982-07-03
IL57182A (en)	1983-07-31
CS211399B2 (en)	1982-02-26
FR2425445B1 (cs)	1984-06-08
EG15150A (en)	1985-12-31
ES480869A1 (es)	1980-06-16
YU108079A (en)	1982-10-31
PL121560B1 (en)	1982-05-31
AT361945B (de)	1981-04-10
DD143765A5 (de)	1980-09-10
NL7903634A (nl)	1979-11-13
DK195279A (da)	1979-11-12
IT7967984A0 (it)	1979-05-10
JPS5522662A (en)	1980-02-18
FI67845B (fi)	1985-02-28
NO791564L (no)	1979-11-13
AR222332A1 (es)	1981-05-15
SU984410A3 (ru)	1982-12-23
FR2425445A1 (fr)	1979-12-07
FI67845C (fi)	1985-06-10
GR68495B (cs)	1982-01-07
CH641437A5 (de)	1984-02-29
DE2917538A1 (de)	1979-11-15
IT1118485B (it)	1986-03-03
SE7904080L (sv)	1979-11-12
GB2024204A (en)	1980-01-09

Legal Events

Date	Code	Title	Description
2000-04-26	MKEX	Expiry

Publication	Publication Date	Title
US4423044A (en)	1983-12-27	3,4-Dihydro-5H-2,3-benzodiazepine derivatives and pharmaceutical use thereof
HU193161B (en)	1987-08-28	Process for preparing new n-alkyl-norscopines
JPS6089474A (ja)	1985-05-20	モルフイナン誘導体，その製造方法，及び該化合物を含有する抗腫瘍剤
EP0005528A2 (en)	1979-11-28	Imidazole derivatives, their preparation and pharmaceutical compositions
CA1149404A (en)	1983-07-05	Substituted oxiranecarboxylic acids, processes for their preparation, their use and medicaments containing them
US4882316A (en)	1989-11-21	Pyrimidine derivatives
CA1145349A (en)	1983-04-26	Terminal bifunktional xylite-derivatives
EP0087655A1 (de)	1983-09-07	Verfahren zur Herstellung von Acemetacin
JPH032116A (ja)	1991-01-08	ベンゼン誘導体、その調製およびこれを含有する薬学的組成物
EP0206021B1 (de)	1988-08-10	Neue Derivate des 1,1,2,2-Tetramethyl-1,2-bis-(2-fluor-4-hydroxyphenyl)-ethans
US3179665A (en)	1965-04-20	9-(n-ethyl and n-propyl piperidyl-3'-methyl)-thioxanthenes
US4059602A (en)	1977-11-22	8-Methyl-, phenyl-, or substituted phenyl-11,12-secoprostaglandins
US4059601A (en)	1977-11-22	8-Halo-11,12-secoprostaglandins
EP0004107B1 (en)	1982-04-07	3-azabicyclo(3.1.0)hexane derivatives, a process for their preparation, biologically active compositions containing them and herbicidal method using them
EP0110575B1 (en)	1987-05-20	1-aroyl-5-oxo-2-pyrrolidinepropanoic acids and related esters
JPS6159308B2 (cs)	1986-12-16
US4673692A (en)	1987-06-16	Diphenylmethylimine derivatives, their compositions and pharmaceutical uses
US4044132A (en)	1977-08-23	Substituted piperazine derivative, its preparation and anorexia compositions containing it
US4734428A (en)	1988-03-29	Aminoethylimidazole and cytoprotective and gastric antisecretory composition containing the same
US3931275A (en)	1976-01-06	Bis(4-(4-hydroxybenzyl)phenyl) carbonic acid ester
JPS6112660A (ja)	1986-01-21	新規２−ピロリドン誘導体及び抗炎症剤
US3341591A (en)	1967-09-12	1-(o-chlorophenyl)-and 1-(o, p-dichlorophenyl)-2-hydrazinopropanes
US3891716A (en)	1975-06-24	Terephenylyl-butadienols
US3925483A (en)	1975-12-09	{60 -(p-benzyloxyphenyl)-p-cresol
US3183246A (en)	1965-05-11	1, 1-dioxothienylcarbamates