HRP980175A2 - Process for preparing o-(3-amino-2-hydroxy-propyl)-hydroxymic acid halides - Google Patents

Process for preparing o-(3-amino-2-hydroxy-propyl)-hydroxymic acid halides

Info

Publication number: HRP980175A2
Authority: HR; Croatia
Prior art keywords: hydroxy; formula; reaction; amino; substituted
Prior art date: 1997-04-03

Application number

HRP9700699A

Other languages

English (en)

Croatian (hr)

Inventor

Zita Csakai

Original Assignee

Biorex Kutatoe Es Fejlesztoe R

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.)

1997-04-03

Filing date

1998-04-03

Publication date

1999-06-30

1998-04-03 Application filed by Biorex Kutatoe Es Fejlesztoe R filed Critical Biorex Kutatoe Es Fejlesztoe R

1999-06-30 Publication of HRP980175A2 publication Critical patent/HRP980175A2/hr

Links

239000002253 acid Substances 0.000 title claims description 12
150000004820 halides Chemical class 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title description 5
238000000034 method Methods 0.000 claims description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 18
-1 carboxamide oxime Chemical class 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 9
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 8
238000006193 diazotization reaction Methods 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical class OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 claims description 5
239000012954 diazonium Substances 0.000 claims description 5
150000001989 diazonium salts Chemical group 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
238000000354 decomposition reaction Methods 0.000 claims description 4
235000010288 sodium nitrite Nutrition 0.000 claims description 4
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical class CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 3
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
238000000926 separation method Methods 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
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 claims description 2
229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims description 2
229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 7
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FXNSRODXMVUCNJ-ODZAUARKSA-N (z)-but-2-enedioic acid;hydrochloride Chemical compound Cl.OC(=O)\C=C/C(O)=O FXNSRODXMVUCNJ-ODZAUARKSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
239000011976 maleic acid Substances 0.000 description 3
AQBMQGDKWIPBRF-UHFFFAOYSA-N n'-hydroxypyridine-3-carboximidamide Chemical compound ON=C(N)C1=CC=CN=C1 AQBMQGDKWIPBRF-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
RPNGOMBXNOMBCG-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-(2-hydroxy-3-piperidin-1-ylpropoxy)pyridine-3-carboximidoyl chloride Chemical compound OC(=O)\C=C/C(O)=O.C1CCCCN1CC(O)CON=C(Cl)C1=CC=CN=C1 RPNGOMBXNOMBCG-BTJKTKAUSA-N 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
239000004593 Epoxy Substances 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
125000001475 halogen functional group Chemical group 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
ZYJPUMXJBDHSIF-NSHDSACASA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 ZYJPUMXJBDHSIF-NSHDSACASA-N 0.000 description 1
IGMZDGBNMCELOE-UHFFFAOYSA-N 1-chloro-3-piperidin-1-ylpropan-2-ol Chemical compound ClCC(O)CN1CCCCC1 IGMZDGBNMCELOE-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
DAXOEPZCJSADTF-UHFFFAOYSA-N Cl.C1CCCCN1CC(O)CON=C(Cl)C1=CC=CS1 Chemical compound Cl.C1CCCCN1CC(O)CON=C(Cl)C1=CC=CS1 DAXOEPZCJSADTF-UHFFFAOYSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
KYAJBRQELLCANX-UHFFFAOYSA-N acetic acid acetylene Chemical compound C#C.CC(O)=O KYAJBRQELLCANX-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
JZHARKPIZHJQHA-UHFFFAOYSA-N n-(2-hydroxy-3-piperidin-1-ylpropoxy)-2-(trifluoromethyl)benzenecarboximidoyl chloride;hydrochloride Chemical compound Cl.C1CCCCN1CC(O)CON=C(Cl)C1=CC=CC=C1C(F)(F)F JZHARKPIZHJQHA-UHFFFAOYSA-N 0.000 description 1
HPNBPCVAJIMXAR-UHFFFAOYSA-N n-(2-hydroxy-3-piperidin-1-ylpropoxy)benzenecarboximidoyl chloride;hydrochloride Chemical compound Cl.C1CCCCN1CC(O)CON=C(Cl)C1=CC=CC=C1 HPNBPCVAJIMXAR-UHFFFAOYSA-N 0.000 description 1
NMOVJBAGBXIKCG-UHFFFAOYSA-N n-(2-hydroxy-3-piperidin-1-ylpropoxy)pyridine-3-carboximidoyl chloride Chemical compound C1CCCCN1CC(O)CON=C(Cl)C1=CC=CN=C1 NMOVJBAGBXIKCG-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
231100000915 pathological change Toxicity 0.000 description 1
230000036285 pathological change Effects 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000000126 substance 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
229930192474 thiophene Natural products 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
230000002792 vascular Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/02—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by halogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Hematology (AREA)
Obesity (AREA)
Endocrinology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Emergency Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

HRP9700699A 1997-04-03 1998-04-03 Process for preparing o-(3-amino-2-hydroxy-propyl)-hydroxymic acid halides HRP980175A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU9700699A HU220971B1 (hu)	1997-04-03	1997-04-03	Eljárás 0-(3-amino-2-hidroxi-propil)-hidroximsav-halogenidek előállítására

Publications (1)

Publication Number	Publication Date
HRP980175A2 true HRP980175A2 (en)	1999-06-30

Family

ID=89994956

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HRP9700699A HRP980175A2 (en)	1997-04-03	1998-04-03	Process for preparing o-(3-amino-2-hydroxy-propyl)-hydroxymic acid halides

Country Status (33)

Country	Link
US (1)	US6180787B1 (fr)
EP (1)	EP0975585A1 (fr)
JP (1)	JP2001521498A (fr)
KR (1)	KR20010005943A (fr)
CN (1)	CN1251574A (fr)
AP (1)	AP9901646A0 (fr)
AR (1)	AR012308A1 (fr)
AU (1)	AU737994B2 (fr)
BG (1)	BG63116B1 (fr)
BR (1)	BR9714717A (fr)
CA (1)	CA2285360A1 (fr)
CO (1)	CO4940491A1 (fr)
EA (1)	EA199900899A1 (fr)
EE (1)	EE03868B1 (fr)
EG (1)	EG22104A (fr)
HR (1)	HRP980175A2 (fr)
HU (1)	HU220971B1 (fr)
ID (1)	ID20016A (fr)
IL (1)	IL132048A0 (fr)
IS (1)	IS5174A (fr)
MA (1)	MA26143A1 (fr)
NO (1)	NO312027B1 (fr)
NZ (1)	NZ500020A (fr)
PE (1)	PE83299A1 (fr)
PL (1)	PL336072A1 (fr)
SK (1)	SK134899A3 (fr)
TN (1)	TNSN98046A1 (fr)
TR (1)	TR199902207T2 (fr)
TW (1)	TW455573B (fr)
UY (1)	UY24945A1 (fr)
WO (1)	WO1998043948A1 (fr)
YU (1)	YU49499A (fr)
ZA (1)	ZA982755B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HUP9900475D0 (en) *	1999-02-26	1999-04-28	Biorex Kutato Fejlesztoe Kft	O-(3-piperidino-2-hydroxy-1-propyl)-hiyroximic acid-halogenid derivative, it's use for treating insulin resistance, and pharmaceutical compositions containing them as active component
JP2005514418A (ja)	2002-01-11	2005-05-19	ビオレックスクタトーエスフェイレストェーアールテー．	カルボキサミジン誘導体及び血管疾患の治療におけるそれらの使用
HUP0303584A3 (en)	2003-10-30	2009-12-28	Cytrx Corp	Use of a hydroximic acid halide derivative in the treatment of neurodegenerative diseases
JP5995988B2 (ja) *	2011-12-23	2016-09-21	アクゾノーベルケミカルズインターナショナルベスローテンフエンノートシャップＡｋｚｏＮｏｂｅｌＣｈｅｍｉｃａｌｓＩｎｔｅｒｎａｔｉｏｎａｌＢ．Ｖ．	化合物
US9422447B2 (en) *	2012-06-14	2016-08-23	Novartis Ag	Azetidinium-containing copolymers and uses thereof
CN103804309B (zh) *	2012-11-09	2019-08-02	广州喜鹊医药有限公司	一种氯肟类化合物及其制备方法和在制药中的应用
KR20230128462A (ko)	2020-11-19	2023-09-05	제브라 덴마크 에이/에스	아리모클로몰 시트레이트 및 이의 중간체를 제조하기 위한 공정

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU207305B (en) *	1988-03-23	1993-03-29	Chinoin Gyogyszer Es Vegyeszet	Improved process for producing amidoxime derivatives
HU207988B (en) *	1988-10-20	1993-07-28	Biorex Kutato Fejlesztoe Kft	Process for producing halogenides of o-/3-amino-2-hydroxy-propyl/hydroximic acid and pharmaceutical compositions containing them as active components
HUT54347A (en) *	1989-01-10	1991-02-28	Chinoin Gyogyszer Es Vegyeszet	Improved process for producing amidoximes

1997
- 1997-04-03 HU HU9700699A patent/HU220971B1/hu not_active IP Right Cessation
- 1997-12-05 AU AU54055/98A patent/AU737994B2/en not_active Ceased
- 1997-12-05 EP EP97947819A patent/EP0975585A1/fr not_active Withdrawn
- 1997-12-05 JP JP54132298A patent/JP2001521498A/ja active Pending
- 1997-12-05 KR KR1019997009020A patent/KR20010005943A/ko not_active Withdrawn
- 1997-12-05 PL PL97336072A patent/PL336072A1/xx unknown
- 1997-12-05 CA CA002285360A patent/CA2285360A1/fr not_active Abandoned
- 1997-12-05 WO PCT/HU1997/000082 patent/WO1998043948A1/fr not_active Ceased
- 1997-12-05 EE EEP199900438A patent/EE03868B1/xx not_active IP Right Cessation
- 1997-12-05 CN CN97182087A patent/CN1251574A/zh active Pending
- 1997-12-05 NZ NZ500020A patent/NZ500020A/en unknown
- 1997-12-05 US US09/402,267 patent/US6180787B1/en not_active Expired - Fee Related
- 1997-12-05 EA EA199900899A patent/EA199900899A1/ru unknown
- 1997-12-05 SK SK1348-99A patent/SK134899A3/sk unknown
- 1997-12-05 TR TR1999/02207T patent/TR199902207T2/xx unknown
- 1997-12-05 BR BR9714717-6A patent/BR9714717A/pt not_active Application Discontinuation
- 1997-12-05 AP APAP/P/1999/001646A patent/AP9901646A0/en unknown
- 1997-12-15 YU YU49499A patent/YU49499A/sh unknown
1998
- 1998-03-30 MA MA25016A patent/MA26143A1/fr unknown
- 1998-03-31 EG EG36098A patent/EG22104A/xx active
- 1998-04-01 ZA ZA982755A patent/ZA982755B/xx unknown
- 1998-04-02 PE PE1998000247A patent/PE83299A1/es not_active Application Discontinuation
- 1998-04-02 TN TNTNSN98046A patent/TNSN98046A1/fr unknown
- 1998-04-02 AR ARP980101495A patent/AR012308A1/es not_active Application Discontinuation
- 1998-04-02 UY UY24945A patent/UY24945A1/es not_active IP Right Cessation
- 1998-04-03 CO CO98018891A patent/CO4940491A1/es unknown
- 1998-04-03 ID IDP980507A patent/ID20016A/id unknown
- 1998-04-03 HR HRP9700699A patent/HRP980175A2/hr not_active Application Discontinuation
- 1998-04-07 TW TW087105087A patent/TW455573B/zh not_active IP Right Cessation
1999
- 1999-09-10 IS IS5174A patent/IS5174A/is unknown
- 1999-09-23 NO NO19994628A patent/NO312027B1/no not_active IP Right Cessation
- 1999-09-23 IL IL13204899A patent/IL132048A0/xx unknown
- 1999-11-02 BG BG103847A patent/BG63116B1/bg unknown

Also Published As

Publication number	Publication date
AR012308A1 (es)	2000-10-18
TNSN98046A1 (fr)	2005-03-15
EP0975585A1 (fr)	2000-02-02
BR9714717A (pt)	2000-06-20
KR20010005943A (ko)	2001-01-15
HUP9700699A2 (hu)	1999-01-28
YU49499A (sh)	2001-09-28
WO1998043948A1 (fr)	1998-10-08
HU220971B1 (hu)	2002-07-29
CN1251574A (zh)	2000-04-26
SK134899A3 (en)	2000-06-12
HU9700699D0 (en)	1997-05-28
NO312027B1 (no)	2002-03-04
EA199900899A1 (ru)	2000-04-24
CA2285360A1 (fr)	1998-10-08
ID20016A (id)	1998-09-10
TW455573B (en)	2001-09-21
IL132048A0 (en)	2001-03-19
UY24945A1 (es)	1998-09-28
HUP9700699A3 (en)	1999-04-28
PE83299A1 (es)	1999-09-01
EE03868B1 (et)	2002-10-15
AU5405598A (en)	1998-10-22
JP2001521498A (ja)	2001-11-06
AU737994B2 (en)	2001-09-06
AP9901646A0 (en)	1999-09-30
NO994628L (no)	1999-09-23
IS5174A (is)	1999-09-10
NO994628D0 (no)	1999-09-23
TR199902207T2 (xx)	2000-02-21
US6180787B1 (en)	2001-01-30
EE9900438A (et)	2000-04-17
EG22104A (en)	2002-07-31
MA26143A1 (fr)	2004-07-01
NZ500020A (en)	2001-09-28
BG103847A (en)	2000-07-31
PL336072A1 (en)	2000-06-05
ZA982755B (en)	1998-10-01
BG63116B1 (bg)	2001-04-30
CO4940491A1 (es)	2000-07-24

Legal Events

Date	Code	Title
1999-06-30	A1OB	Publication of a patent application
1999-12-30	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2003-06-17	ODBC	Application rejected

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