FI67845C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara xylitolderivat - Google Patents

Foerfarande foer framstaellning av nya terapeutiskt anvaendbara xylitolderivat Download PDF

Info

Publication number: FI67845C
Authority: FI; Finland
Prior art keywords: formula; halogen; defined above; xylitol; phenyl
Prior art date: 1978-05-11

Application number

FI791484A

Other languages

English (en)

Finnish (fi)

Other versions

FI791484A7 (fi

FI67845B (fi

Inventor

Nee Sandor Ildiko Vidra

Laszlo Institoris

Sandor Eckhardt

Karoly Lapis

Andras Jeney

Laszlo Kopper

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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

1979-05-09

Publication date

1985-06-10

1979-05-09 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1979-11-12 Publication of FI791484A7 publication Critical patent/FI791484A7/fi

1985-02-28 Application granted granted Critical

1985-02-28 Publication of FI67845B publication Critical patent/FI67845B/fi

1985-06-10 Publication of FI67845C publication Critical patent/FI67845C/fi

Links

230000001225 therapeutic effect Effects 0.000 title claims 2
238000002560 therapeutic procedure Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 14
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 9
239000000811 xylitol Substances 0.000 claims description 9
229960002675 xylitol Drugs 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
239000002516 radical scavenger Substances 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
238000000034 method Methods 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
241000251730 Chondrichthyes Species 0.000 claims description 2
230000010933 acylation Effects 0.000 claims description 2
238000005917 acylation reaction Methods 0.000 claims description 2
229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 3
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
125000000217 alkyl group Chemical group 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 25
241001465754 Metazoa Species 0.000 description 16
241000699670 Mus sp. Species 0.000 description 14
-1 sugar alcohol compounds Chemical class 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
206010028980 Neoplasm Diseases 0.000 description 10
239000000203 mixture Substances 0.000 description 10
238000002054 transplantation Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000002474 experimental method Methods 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 7
238000011282 treatment Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
235000010447 xylitol Nutrition 0.000 description 6
230000001085 cytostatic effect Effects 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
239000003380 propellant Substances 0.000 description 4
230000004083 survival effect Effects 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
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 description 2
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
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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 2
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 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
206010061968 Gastric neoplasm Diseases 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
239000000654 additive Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
239000000843 powder Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 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
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-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 compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical class OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 1
239000004593 Epoxy 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
208000007093 Leukemia L1210 Diseases 0.000 description 1
241001529936 Murinae Species 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
125000004036 acetal group Chemical group 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000006071 cream 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
239000003480 eluent Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000012010 growth Effects 0.000 description 1
201000005787 hematologic cancer Diseases 0.000 description 1
208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
231100000171 higher toxicity Toxicity 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000011021 lapis lazuli Substances 0.000 description 1
208000020816 lung neoplasm Diseases 0.000 description 1
208000037841 lung tumor Diseases 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
239000002674 ointment Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000011458 pharmacological treatment Methods 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
230000002000 scavenging effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 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
150000003512 tertiary amines Chemical class 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
230000004614 tumor growth Effects 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Epoxy Compounds (AREA)

FI791484A 1978-05-11 1979-05-09 Foerfarande foer framstaellning av nya terapeutiskt anvaendbara xylitolderivat FI67845C (fi)

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
HUCI001826		1978-05-11

Publications (3)

Publication Number	Publication Date
FI791484A7 FI791484A7 (fi)	1979-11-12
FI67845B FI67845B (fi)	1985-02-28
FI67845C true FI67845C (fi)	1985-06-10

Family

ID=10994695

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI791484A FI67845C (fi)	1978-05-11	1979-05-09	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara xylitolderivat

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 IL IL57182A patent/IL57182A/xx unknown
- 1979-04-30 DE DE19792917538 patent/DE2917538A1/de not_active Withdrawn
- 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 NL NL7903634A patent/NL7903634A/xx not_active Application Discontinuation
- 1979-05-09 FR FR7911733A patent/FR2425445A1/fr active Granted
- 1979-05-09 YU YU01080/79A patent/YU108079A/xx unknown
- 1979-05-09 FI FI791484A patent/FI67845C/fi not_active IP Right Cessation
- 1979-05-09 SE SE7904080A patent/SE7904080L/xx not_active Application Discontinuation
- 1979-05-10 BE BE0/195089A patent/BE876166A/xx not_active IP Right Cessation
- 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 PL PL1979215489A patent/PL121560B1/pl unknown
- 1979-05-10 JP JP5758879A patent/JPS5522662A/ja active Pending
- 1979-05-10 CH CH438979A patent/CH641437A5/de not_active IP Right Cessation
- 1979-05-10 CA CA000327317A patent/CA1145349A/en not_active Expired
- 1979-05-10 CS CS793205A patent/CS211399B2/cs unknown
- 1979-05-10 NO NO791564A patent/NO153928C/no unknown
- 1979-05-10 GB GB7916274A patent/GB2024204B/en not_active Expired
- 1979-05-10 DK DK195279A patent/DK195279A/da not_active Application Discontinuation
- 1979-05-10 AR AR276464A patent/AR222332A1/es active
- 1979-05-11 DD DD79212780A patent/DD143765A5/de unknown
- 1979-05-11 SU SU792764801A patent/SU984410A3/ru active
- 1979-05-11 ES ES480869A patent/ES480869A1/es not_active Expired

Also Published As

Publication number	Publication date
ES480869A1 (es)	1980-06-16
SU984410A3 (ru)	1982-12-23
AT361945B (de)	1981-04-10
EG15150A (en)	1985-12-31
FR2425445B1 (cs)	1984-06-08
DD143765A5 (de)	1980-09-10
ATA347779A (de)	1980-09-15
GB2024204A (en)	1980-01-09
IL57182A (en)	1983-07-31
FI791484A7 (fi)	1979-11-12
JPS5522662A (en)	1980-02-18
CS211399B2 (en)	1982-02-26
SE7904080L (sv)	1979-11-12
FR2425445A1 (fr)	1979-12-07
CH641437A5 (de)	1984-02-29
IT1118485B (it)	1986-03-03
HU176216B (en)	1981-01-28
GR68495B (cs)	1982-01-07
NO791564L (no)	1979-11-13
GB2024204B (en)	1982-10-27
NO153928B (no)	1986-03-10
PL121560B1 (en)	1982-05-31
DE2917538A1 (de)	1979-11-15
IT7967984A0 (it)	1979-05-10
NL7903634A (nl)	1979-11-13
IL57182A0 (en)	1979-07-25
YU108079A (en)	1982-10-31
FI67845B (fi)	1985-02-28
NO153928C (no)	1986-06-18
PL215489A1 (cs)	1980-02-11
DK195279A (da)	1979-11-12
AR222332A1 (es)	1981-05-15
BE876166A (fr)	1979-09-03
CA1145349A (en)	1983-04-26
IN150040B (cs)	1982-07-03

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: CHINOIN GYOGUSZER ES VEGYESZETI TERMEKEK

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NO175620B (cs)	1994-08-01
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US4268676A (en)	1981-05-19	Mitomycin analogs
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JPS6260393B2 (cs)	1987-12-16
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US4892939A (en)	1990-01-09	Oligopeptidyl-5-fluorouridine compounds and process for preparing the same
FI71934B (fi)	1986-11-28	Foerfarande foer framstaellning av nya n-substituerade polyglycidyl-urazolfoereningar
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US4576945A (en)	1986-03-18	Hexaalkylmelamine-amino-oxy compounds
FI85140C (fi)	1992-03-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara n-(1h-indol-4-yl)-bensamidderivat.
US3996284A (en)	1976-12-07	Naphthyl and tetrahydronaphthyl di-ethers