NO309812B1 - Makrocykliske forbindelser, fremgangsmÕte ved fremstilling derav, anvendelse derav og farmasøytisk preparat inneholdende slike - Google Patents

Makrocykliske forbindelser, fremgangsmÕte ved fremstilling derav, anvendelse derav og farmasøytisk preparat inneholdende slike Download PDF

Info

Publication number: NO309812B1
Authority: NO; Norway
Prior art keywords: methylene; phenylenebis; tetraazacyclotetradecanyl; compound; formula
Prior art date: 1995-06-06

Application number

NO962325A

Other languages

English (en)

Norwegian (no)

Other versions

NO962325D0 (no

NO962325L (no

Inventor

Gary James Bridger

Sreenivasan Padmanabhan

Renato Tony Skerlj

Pedro Emilio Hernandez-Abad

Milind Prabhakar Sant

Original Assignee

Anormed Inc

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.)

1995-06-06

Filing date

1996-06-05

Publication date

2001-04-02

1996-06-05 Application filed by Anormed Inc filed Critical Anormed Inc

1996-06-05 Publication of NO962325D0 publication Critical patent/NO962325D0/no

1996-12-09 Publication of NO962325L publication Critical patent/NO962325L/no

2001-04-02 Publication of NO309812B1 publication Critical patent/NO309812B1/no

Links

238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 12
239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
150000002678 macrocyclic compounds Chemical class 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 50
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 18
238000011282 treatment Methods 0.000 claims description 11
-1 5-methylpyrazinyl Chemical group 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
MDAXKAUIABOHTD-UHFFFAOYSA-N 1,4,8,11-tetraazacyclotetradecane Chemical compound C1CNCCNCCCNCCNC1 MDAXKAUIABOHTD-UHFFFAOYSA-N 0.000 claims description 6
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
238000010511 deprotection reaction Methods 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
230000000269 nucleophilic effect Effects 0.000 claims description 5
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
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 description 3
230000001225 therapeutic effect Effects 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
150000002460 imidazoles Chemical class 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
YRMKTQNDPSHONR-UHFFFAOYSA-N 1-phenyl-n-[[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methyl]methanamine Chemical compound C=1C=CC=CC=1CNCC(C=C1)=CC=C1CN1CCCNCCNCCCNCC1 YRMKTQNDPSHONR-UHFFFAOYSA-N 0.000 claims 1
UQJUPEBNPXJTGH-UHFFFAOYSA-N 2-[[[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methylamino]methyl]aniline Chemical compound NC1=CC=CC=C1CNCC(C=C1)=CC=C1CN1CCNCCCNCCNCCC1 UQJUPEBNPXJTGH-UHFFFAOYSA-N 0.000 claims 1
WRXILBMKDNKDQT-UHFFFAOYSA-N 4-[[[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methylamino]methyl]aniline Chemical compound C1=CC(N)=CC=C1CNCC(C=C1)=CC=C1CN1CCNCCCNCCNCCC1 WRXILBMKDNKDQT-UHFFFAOYSA-N 0.000 claims 1
125000002883 imidazolyl group Chemical group 0.000 claims 1
239000004615 ingredient Substances 0.000 claims 1
CWJJHESJXJQCJA-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-1-[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methanamine Chemical group C=1C=C(CN2CCNCCCNCCNCCC2)C=CC=1CNCC1=CC=CC=N1 CWJJHESJXJQCJA-UHFFFAOYSA-N 0.000 claims 1
TWTLJZJKDUYSON-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)-1-[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methanamine Chemical compound C=1C=C(CN2CCNCCCNCCNCCC2)C=CC=1CNCC1=CC=CN=C1 TWTLJZJKDUYSON-UHFFFAOYSA-N 0.000 claims 1
RTHCDPLDSUOFCC-UHFFFAOYSA-N n-(pyridin-4-ylmethyl)-1-[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methanamine Chemical compound C=1C=NC=CC=1CNCC(C=C1)=CC=C1CN1CCCNCCNCCCNCC1 RTHCDPLDSUOFCC-UHFFFAOYSA-N 0.000 claims 1
125000003373 pyrazinyl group Chemical group 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
238000005481 NMR spectroscopy Methods 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 14
239000007787 solid Substances 0.000 description 14
238000004458 analytical method Methods 0.000 description 12
239000000243 solution Substances 0.000 description 8
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
241000725303 Human immunodeficiency virus Species 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
238000012360 testing method Methods 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
229920000768 polyamine Polymers 0.000 description 5
241000713772 Human immunodeficiency virus 1 Species 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
208000030507 AIDS Diseases 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
241000700605 Viruses Species 0.000 description 3
239000000654 additive Substances 0.000 description 3
230000000840 anti-viral effect Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
NXTXXDXIVHAEQF-UHFFFAOYSA-N 1-diethoxyphosphoryl-1,4,8,11-tetrazacyclotetradecane Chemical compound CCOP(=O)(OCC)N1CCCNCCNCCCNCC1 NXTXXDXIVHAEQF-UHFFFAOYSA-N 0.000 description 2
229910004373 HOAc Inorganic materials 0.000 description 2
241000713340 Human immunodeficiency virus 2 Species 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
210000001124 body fluid Anatomy 0.000 description 2
239000010839 body fluid Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000011835 investigation Methods 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000651 prodrug Substances 0.000 description 2
229940002612 prodrug Drugs 0.000 description 2
239000000047 product Substances 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
WGOJMUSSYPZTBW-UHFFFAOYSA-N (diethoxyamino)phosphonic acid Chemical group CCON(P(O)(O)=O)OCC WGOJMUSSYPZTBW-UHFFFAOYSA-N 0.000 description 1
GEYHEZYCYIFNBW-UHFFFAOYSA-N 1,4,8-tris(diethoxyphosphoryl)-1,4,8,11-tetrazacyclotetradecane Chemical compound CCOP(=O)(OCC)N1CCCN(P(=O)(OCC)OCC)CCN(P(=O)(OCC)OCC)CCCNCC1 GEYHEZYCYIFNBW-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RBZMSGOBSOCYHR-UHFFFAOYSA-N 1,4-bis(bromomethyl)benzene Chemical group BrCC1=CC=C(CBr)C=C1 RBZMSGOBSOCYHR-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
206010001513 AIDS related complex Diseases 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
208000031886 HIV Infections Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
CTGZSPZNEVSQEJ-UHFFFAOYSA-N O.O.Br.Br.Br.Br.Br Chemical compound O.O.Br.Br.Br.Br.Br CTGZSPZNEVSQEJ-UHFFFAOYSA-N 0.000 description 1
206010038997 Retroviral infections Diseases 0.000 description 1
208000005074 Retroviridae Infections Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
208000036142 Viral infection Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
231100000135 cytotoxicity Toxicity 0.000 description 1
230000003013 cytotoxicity Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000009510 drug design Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
210000005260 human cell Anatomy 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
238000004393 prognosis Methods 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000011160 research Methods 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
238000010898 silica gel chromatography Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000003892 spreading Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
241001430294 unidentified retrovirus Species 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D255/00—Heterocyclic compounds containing rings having three nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D249/00 - C07D253/00
- C07D255/02—Heterocyclic compounds containing rings having three nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D249/00 - C07D253/00 not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D259/00—Heterocyclic compounds containing rings having more than four nitrogen atoms as the only ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Virology (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Oncology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Mechanical Coupling Of Light Guides (AREA)
Earth Drilling (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pyridine Compounds (AREA)

NO962325A 1995-06-06 1996-06-05 Makrocykliske forbindelser, fremgangsmÕte ved fremstilling derav, anvendelse derav og farmasøytisk preparat inneholdende slike NO309812B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB9511357.7A GB9511357D0 (en)	1995-06-06	1995-06-06	Improved antiviral compounds

Publications (3)

Publication Number	Publication Date
NO962325D0 NO962325D0 (no)	1996-06-05
NO962325L NO962325L (no)	1996-12-09
NO309812B1 true NO309812B1 (no)	2001-04-02

Family

ID=10775536

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO962325A NO309812B1 (no)	1995-06-06	1996-06-05	Makrocykliske forbindelser, fremgangsmÕte ved fremstilling derav, anvendelse derav og farmasøytisk preparat inneholdende slike

Country Status (13)

Country	Link
US (1)	US5817807A (fr)
EP (1)	EP0747368B1 (fr)
JP (1)	JP3510955B2 (fr)
KR (1)	KR100420725B1 (fr)
AT (1)	ATE360623T1 (fr)
AU (1)	AU713320B2 (fr)
CA (1)	CA2178272C (fr)
DE (1)	DE69637040T2 (fr)
GB (1)	GB9511357D0 (fr)
NO (1)	NO309812B1 (fr)
NZ (1)	NZ286711A (fr)
TW (1)	TW467744B (fr)
ZA (1)	ZA964548B (fr)

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JP2008509928A (ja) *	2004-08-13	2008-04-03	アノーメドインコーポレイテッド	前駆／幹細胞を動員するためのケモカインの組み合わせ
TW200619206A (en) *	2004-09-29	2006-06-16	Anormed Inc	Chemokine-binding heterocyclic compound salts, and methods of use thereof
EP1942890A4 (fr) *	2005-06-15	2009-08-26	Genzyme Corp	Composes de liaison au recepteur de la chimiokine
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RU2638802C2 (ru)	2011-05-16	2017-12-15	Джензим Корпорейшн	Применение антагонистов cxcr4
PT2794626T (pt)	2011-12-22	2018-01-12	Glycomimetics Inc	Compostos de antagonistas de e-selectina
CA2891514C (fr)	2012-12-07	2020-08-25	Glycomimetics, Inc.	Composes, compositions et procedes utilisant des antagonistes d'e-selectine pour la mobilisation de cellules hematopoietiques
ES2754549T3 (es)	2014-12-03	2020-04-20	Glycomimetics Inc	Inhibidores heterobifuncionales de E-selectinas y receptores de quimioquinas CXCR4
CA3026154A1 (fr)	2015-06-03	2016-12-08	The University Of Queensland	Agents mobilisateurs et leurs utilisations
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CN109069426B (zh)	2015-12-14	2021-10-29	X4 制药有限公司	治疗癌症的方法
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US11337969B2 (en)	2016-04-08	2022-05-24	X4 Pharmaceuticals, Inc.	Methods for treating cancer
CN109640988A (zh)	2016-06-21	2019-04-16	X4 制药有限公司	Cxcr4抑制剂及其用途
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1995
- 1995-06-06 GB GBGB9511357.7A patent/GB9511357D0/en active Pending
1996
- 1996-05-21 DE DE69637040T patent/DE69637040T2/de not_active Expired - Fee Related
- 1996-05-21 AT AT96303608T patent/ATE360623T1/de not_active IP Right Cessation
- 1996-05-21 EP EP96303608A patent/EP0747368B1/fr not_active Expired - Lifetime
- 1996-05-23 AU AU52455/96A patent/AU713320B2/en not_active Ceased
- 1996-05-31 NZ NZ286711A patent/NZ286711A/en not_active IP Right Cessation
- 1996-06-03 ZA ZA964548A patent/ZA964548B/xx unknown
- 1996-06-04 JP JP14179296A patent/JP3510955B2/ja not_active Expired - Fee Related
- 1996-06-05 KR KR1019960019946A patent/KR100420725B1/ko not_active Expired - Fee Related
- 1996-06-05 NO NO962325A patent/NO309812B1/no not_active IP Right Cessation
- 1996-06-05 CA CA002178272A patent/CA2178272C/fr not_active Expired - Fee Related
- 1996-06-06 TW TW085106777A patent/TW467744B/zh not_active IP Right Cessation
- 1996-06-06 US US08/659,500 patent/US5817807A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
AU5245596A (en)	1996-12-19
JP3510955B2 (ja)	2004-03-29
JPH0912560A (ja)	1997-01-14
CA2178272A1 (fr)	1996-12-07
DE69637040T2 (de)	2007-12-27
EP0747368A1 (fr)	1996-12-11
HK1013995A1 (en)	1999-09-17
NO962325D0 (no)	1996-06-05
ATE360623T1 (de)	2007-05-15
AU713320B2 (en)	1999-11-25
KR970000250A (ko)	1997-01-21
ZA964548B (en)	1996-12-12
CA2178272C (fr)	2003-12-16
EP0747368B1 (fr)	2007-04-25
GB9511357D0 (en)	1995-08-02
US5817807A (en)	1998-10-06
KR100420725B1 (ko)	2004-06-12
DE69637040D1 (de)	2007-06-06
TW467744B (en)	2001-12-11
NO962325L (no)	1996-12-09
NZ286711A (en)	1998-02-26

Legal Events

Date	Code	Title	Description
2016-01-25	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO309812B1 (no)	2001-04-02	Makrocykliske forbindelser, fremgangsmÕte ved fremstilling derav, anvendelse derav og farmasøytisk preparat inneholdende slike
US5698546A (en)	1997-12-16	Cyclic polyamines
US5583131A (en)	1996-12-10	Aromatic-linked polyamine macrocyclic compounds with anti-HIV activity
JP3447292B2 (ja)	2003-09-16	イミダゾピリジン及び胃腸の疾病の治療のためのその使用
CZ295618B6 (cs)	2005-09-14	Pyrazinové deriváty, způsob výroby a farmaceutický prostředek
EP2367809B1 (fr)	2013-03-13	Dérivés de [(3-hydroxy-4 pyron-2-yl)méthyl]-amine et leurs utilisations en tant que médicaments anti-néoplasiques
CA2046874C (fr)	1999-03-23	Derives de la n-phenylbenzamide avec pouvoir anti-ulcere et anti-allergique, et methode de preparation
CN106928206A (zh)	2017-07-07	醛基类化合物及其制法和用途
KR20030008151A (ko)	2003-01-24	이미다조피리딘 및 이미다조피리미딘 항바이러스제
WO2018109786A1 (fr)	2018-06-21	Nouveaux polymorphes et sels de dérivés de carbamoyle pyridone polycycliques
NO309567B1 (no)	2001-02-19	Fremgangsmåte for fremstilling av 1,1'-[1,4-fenylenbis-
KR900001194B1 (ko)	1990-02-28	N-아미노피리디늄 베타인 유도체의 제조방법
DK168386B1 (da)	1994-03-21	N-(23-vinblastinoyl)derivater af 1-aminomethylphosphonsyre og en fremgangsmåde til deres fremstilling
WO1992016494A1 (fr)	1992-10-01	Composes antiviraux a longue chaine
US4521606A (en)	1985-06-04	5-Indolyl substituted aminoethanols
US4562200A (en)	1985-12-31	5(Indolyl) and 5(2,3-dihydroindolyl) substituted aminoethanols and their use as anti-hypertensives
JPS62212386A (ja)	1987-09-18	２−ピリジルメチルベンズイミダゾ−ル誘導体
JP3009716B2 (ja)	2000-02-14	新規なカンプトテシン誘導体
CN120842170B (zh)	2026-01-27	一种可降解双子吗啉季铵盐及其制备方法、应用
DK158463B (da)	1990-05-21	Analogifremgangsmaade til fremstilling af glycerol-1,2-bis-aminoalkylethere
HK1013995B (en)	2008-03-07	Derivatives of monocyclic polyamines, their preparation, and their use as antiviral agents
US4622399A (en)	1986-11-11	Bicyclo-heterocyclic nitrogen substituted aminoethanol derivatives
HK40101381B (zh)	2024-08-09	一种抗流感病毒衍生物及其用途
HK40101381A (zh)	2024-05-17	一种抗流感病毒衍生物及其用途
ES2298077A1 (es)	2008-05-01	Nuevos sistemas polintrogenados como agentes anti -vih.