CN1035112C - 用于生产二嗪基哌啶衍生物的改进方法 - Google Patents

用于生产二嗪基哌啶衍生物的改进方法 Download PDF

Info

Publication number: CN1035112C
Authority: CN; China
Prior art keywords: diazine; described method; pyrrolidone; formula; compound
Prior art date: 1989-10-27
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 - Lifetime

Application number

CN90108728A

Other languages

English (en)

Chinese (zh)

Other versions

CN1051357A (zh

Inventor

加里·D·马丁

约瑟夫·L·米尼利

罗纳德·J·马特森

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.)

Bristol Myers Squibb Co

Original Assignee

Bristol Myers Squibb Co

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.)

1989-10-27

Filing date

1990-10-25

Publication date

1997-06-11

1990-10-25 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

1991-05-15 Publication of CN1051357A publication Critical patent/CN1051357A/zh

1997-06-11 Application granted granted Critical

1997-06-11 Publication of CN1035112C publication Critical patent/CN1035112C/zh

2005-10-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 73
230000008569 process Effects 0.000 title abstract description 21
SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims abstract description 15
239000000203 mixture Substances 0.000 claims abstract description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 12
239000003153 chemical reaction reagent Substances 0.000 claims abstract description 11
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims abstract description 10
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims abstract description 10
239000007864 aqueous solution Substances 0.000 claims abstract description 8
229910000104 sodium hydride Inorganic materials 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 6
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims abstract description 5
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims abstract description 5
239000000725 suspension Substances 0.000 claims abstract description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 4
239000012312 sodium hydride Substances 0.000 claims abstract description 4
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 13
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 13
-1 diazine piperidines Chemical class 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 5
238000003786 synthesis reaction Methods 0.000 claims description 5
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
150000001721 carbon Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
150000003053 piperidines Chemical class 0.000 claims description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
230000006872 improvement Effects 0.000 abstract description 8
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
125000004432 carbon atom Chemical group C* 0.000 abstract 1
230000002490 cerebral effect Effects 0.000 abstract 1
150000004891 diazines Chemical class 0.000 abstract 1
239000000047 product Substances 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000243 solution Substances 0.000 description 14
239000000543 intermediate Substances 0.000 description 9
230000004048 modification Effects 0.000 description 9
238000012986 modification Methods 0.000 description 9
238000003756 stirring Methods 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 5
238000010189 synthetic method Methods 0.000 description 5
NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 4
239000006260 foam Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
238000001291 vacuum drying Methods 0.000 description 4
ROGIKWDBLZYABK-UHFFFAOYSA-N 1-(pyridin-4-ylmethyl)pyrrolidin-2-one Chemical compound O=C1CCCN1CC1=CC=NC=C1 ROGIKWDBLZYABK-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
125000002015 acyclic group Chemical group 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000004364 calculation method Methods 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
OVEGSCLVOXWLIV-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=NC=CC(Cl)=N1 OVEGSCLVOXWLIV-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
238000010521 absorption reaction Methods 0.000 description 2
238000009825 accumulation Methods 0.000 description 2
230000003925 brain function Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
230000002045 lasting effect Effects 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000008399 tap water Substances 0.000 description 2
235000020679 tap water Nutrition 0.000 description 2
LZAYRLDDBVAEHL-UHFFFAOYSA-N 1-[(1-pyrimidin-2-ylpiperidin-4-yl)methyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CC1CCN(C=2N=CC=CN=2)CC1 LZAYRLDDBVAEHL-UHFFFAOYSA-N 0.000 description 1
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
NDNXTOYJPCXQBT-UHFFFAOYSA-N 1-[[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]methyl]pyrrolidin-2-one Chemical compound ClC1=NC=CC(N2CCC(CN3C(CCC3)=O)CC2)=N1 NDNXTOYJPCXQBT-UHFFFAOYSA-N 0.000 description 1
JVQLRYRCSOTTOU-UHFFFAOYSA-N 1-[[1-(6-chloropyrazin-2-yl)piperidin-4-yl]methyl]pyrrolidin-2-one Chemical compound ClC1=CN=CC(N2CCC(CN3C(CCC3)=O)CC2)=N1 JVQLRYRCSOTTOU-UHFFFAOYSA-N 0.000 description 1
SGBGKRCKWFSTHS-UHFFFAOYSA-N 1-[[1-(6-chloropyridazin-3-yl)piperidin-4-yl]methyl]pyrrolidin-2-one Chemical compound N1=NC(Cl)=CC=C1N1CCC(CN2C(CCC2)=O)CC1 SGBGKRCKWFSTHS-UHFFFAOYSA-N 0.000 description 1
OPVPRJXJXNNHKB-UHFFFAOYSA-N 1-[[1-(6-chloropyrimidin-4-yl)piperidin-4-yl]methyl]pyrrolidin-2-one Chemical compound C1=NC(Cl)=CC(N2CCC(CN3C(CCC3)=O)CC2)=N1 OPVPRJXJXNNHKB-UHFFFAOYSA-N 0.000 description 1
BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 1
ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical class Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
208000000044 Amnesia Diseases 0.000 description 1
208000031091 Amnestic disease Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
238000007605 air drying Methods 0.000 description 1
230000006986 amnesia Effects 0.000 description 1
125000000129 anionic group Chemical class 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
238000013459 approach Methods 0.000 description 1
230000008901 benefit Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
238000012824 chemical production Methods 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
238000005352 clarification Methods 0.000 description 1
230000003931 cognitive performance Effects 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000007850 degeneration Effects 0.000 description 1
125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 1
238000007599 discharging Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
238000002386 leaching Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000000199 molecular distillation Methods 0.000 description 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
150000003953 γ-lactams Chemical class 0.000 description 1

Classifications

- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pyrrole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CN90108728A 1989-10-27 1990-10-25 用于生产二嗪基哌啶衍生物的改进方法 Expired - Lifetime CN1035112C (zh)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date
US42838289A	1989-10-27	1989-10-27
US428,382		1989-10-27
US58558990A	1990-09-20	1990-09-20
US585,589		1990-09-20
US585589		1990-09-20

Publications (2)

Publication Number	Publication Date
CN1051357A CN1051357A (zh)	1991-05-15
CN1035112C true CN1035112C (zh)	1997-06-11

Family

ID=27027734

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN90108728A Expired - Lifetime CN1035112C (zh)	1989-10-27	1990-10-25	用于生产二嗪基哌啶衍生物的改进方法

Country Status (9)

Country	Link
KR (1)	KR910007913A (de)
CN (1)	CN1035112C (de)
AT (1)	AT398972B (de)
ES (1)	ES2026060A6 (de)
FI (1)	FI95468C (de)
GR (1)	GR1001134B (de)
NO (1)	NO176715C (de)
PT (1)	PT95712B (de)
YU (1)	YU203390A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100432283B1 (ko) *	2001-10-27	2004-05-22	한국과학기술연구원	무스카린성 아세틸콜린 수용체에 작용하는테트라하이드로피리딘 유도체
KR20200047989A (ko)	2018-10-29	2020-05-08	이수완	튜닝이 용이한 바이올린

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4826843A (en) *	1985-07-08	1989-05-02	Bristol-Myers	Cerebral function enhancing diazinylpiperidine derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU206878B (en) *	1989-10-27	1993-01-28	Bristol Myers Squibb Co	Process for producing 1-//1-/2-/trifluoromethyl/-4-pyrimidinyl/-4-piperidinyl/-methyl/-2-pirrolidinone

1990
- 1990-10-24 AT AT0214890A patent/AT398972B/de not_active IP Right Cessation
- 1990-10-24 FI FI905226A patent/FI95468C/fi active IP Right Grant
- 1990-10-24 NO NO904588A patent/NO176715C/no not_active IP Right Cessation
- 1990-10-25 CN CN90108728A patent/CN1035112C/zh not_active Expired - Lifetime
- 1990-10-26 PT PT95712A patent/PT95712B/pt not_active IP Right Cessation
- 1990-10-26 ES ES9002731A patent/ES2026060A6/es not_active Expired - Fee Related
- 1990-10-26 YU YU203390A patent/YU203390A/sh unknown
- 1990-10-26 KR KR1019900017244A patent/KR910007913A/ko not_active Withdrawn
- 1990-10-29 GR GR900100777A patent/GR1001134B/el not_active IP Right Cessation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4826843A (en) *	1985-07-08	1989-05-02	Bristol-Myers	Cerebral function enhancing diazinylpiperidine derivatives

Also Published As

Publication number	Publication date
GR900100777A (en)	1992-03-20
KR910007913A (ko)	1991-05-30
PT95712A (pt)	1991-09-13
ES2026060A6 (es)	1992-04-01
NO176715B (no)	1995-02-06
YU203390A (sh)	1993-10-20
NO176715C (no)	1995-05-16
FI95468B (fi)	1995-10-31
ATA214890A (de)	1994-07-15
FI95468C (fi)	1996-02-12
PT95712B (pt)	1998-01-30
CN1051357A (zh)	1991-05-15
AT398972B (de)	1995-02-27
GR1001134B (el)	1993-04-28
NO904588D0 (no)	1990-10-24
FI905226A0 (fi)	1990-10-24
NO904588L (no)	1991-04-29

Legal Events

Date	Code	Title	Description
1991-05-15	C06	Publication
1991-05-15	PB01	Publication
1993-02-03	C10	Entry into substantive examination
1993-02-03	SE01	Entry into force of request for substantive examination
1997-06-11	C14	Grant of patent or utility model
1997-06-11	GR01	Patent grant
2002-04-24	C15	Extension of patent right duration from 15 to 20 years for appl. with date before 31.12.1992 and still valid on 11.12.2001 (patent law change 1993)
2002-04-24	OR01	Other related matters
2010-12-15	C17	Cessation of patent right
2010-12-15	CX01	Expiry of patent term	Expiration termination date: 20101025 Granted publication date: 19970611

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