LT3532B - Novel pilocarpine derivatives and process for their preparation - Google Patents

Novel pilocarpine derivatives and process for their preparation Download PDF

Info

Publication number: LT3532B
Authority: LT; Lithuania
Prior art keywords: formula; compound; bispilocarpate; acid; mmol
Prior art date: 1990-11-30

Application number

LTIP577A

Other languages

English (en)

Lithuanian (lt)

Inventor

Tomi Jaervinen

Pekka Peura

Pekka Suhonen

Arto Urtti

Hannu Hanhijaervi

Esko Pohjala

Original Assignee

Leiras Oy

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.)

1990-11-30

Filing date

1993-05-28

Publication date

1995-11-27

1993-05-28 Application filed by Leiras Oy filed Critical Leiras Oy

1994-12-27 Publication of LTIP577A publication Critical patent/LTIP577A/xx

1995-11-27 Publication of LT3532B publication Critical patent/LT3532B/lt

Links

238000000034 method Methods 0.000 title claims description 22
238000002360 preparation method Methods 0.000 title claims description 8
230000008569 process Effects 0.000 title claims description 3
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125000003118 aryl group Chemical group 0.000 claims abstract description 10
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239000002253 acid Substances 0.000 claims description 25
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230000008901 benefit Effects 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000036471 bradycardia Effects 0.000 description 1
208000006218 bradycardia Diseases 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
239000007853 buffer solution Substances 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
210000000795 conjunctiva Anatomy 0.000 description 1
239000006071 cream Substances 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
125000004976 cyclobutylene group Chemical group 0.000 description 1
125000004979 cyclopentylene group Chemical group 0.000 description 1
125000004980 cyclopropylene group Chemical group 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002651 drug therapy Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000003511 endothelial effect Effects 0.000 description 1
210000005081 epithelial layer Anatomy 0.000 description 1
210000000981 epithelium Anatomy 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
150000002634 lipophilic molecules Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
229940041033 macrolides Drugs 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004957 naphthylene group Chemical group 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
YVOFTMXWTWHRBH-UHFFFAOYSA-N pentanedioyl dichloride Chemical compound ClC(=O)CCCC(Cl)=O YVOFTMXWTWHRBH-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
230000035699 permeability Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
235000019515 salmon Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Ophthalmology & Optometry (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

LTIP577A 1990-11-30 1993-05-28 Novel pilocarpine derivatives and process for their preparation LT3532B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FI905930A FI98815C (fi)	1990-11-30	1990-11-30	Menetelmä uusien, farmakologisesti käyttökelpoisten bispilokarpiinihapon esterijohdannaisten valmistamiseksi

Publications (2)

Publication Number	Publication Date
LTIP577A LTIP577A (en)	1994-12-27
LT3532B true LT3532B (en)	1995-11-27

Family

ID=8531500

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP577A LT3532B (en)	1990-11-30	1993-05-28	Novel pilocarpine derivatives and process for their preparation

Country Status (19)

Country	Link
EP (1)	EP0559700B1 (de)
JP (1)	JP3094232B2 (de)
KR (1)	KR930703264A (de)
AT (1)	ATE192144T1 (de)
AU (1)	AU664958B2 (de)
CA (1)	CA2096444A1 (de)
CZ (1)	CZ282229B6 (de)
DE (1)	DE69132143T2 (de)
EE (1)	EE9400143A (de)
FI (1)	FI98815C (de)
HU (1)	HUT67273A (de)
LT (1)	LT3532B (de)
LV (1)	LV10094B (de)
NO (1)	NO304228B1 (de)
NZ (1)	NZ240781A (de)
PL (2)	PL168715B1 (de)
RU (1)	RU2100352C1 (de)
SK (1)	SK52393A3 (de)
WO (1)	WO1992009583A1 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0642501A1 (de) *	1992-05-29	1995-03-15	Leiras Oy	Neue pilocarpin-derivate und verfahren zu deren herstellung
GB9310965D0 (en) *	1993-05-27	1993-07-14	Ucb Sa	2-hydroxy-3-(1h-imidazol-4-yl)alkyl)benzenecarboximidamides
AU6973094A (en) *	1993-06-24	1995-01-17	Leiras Oy	Composition for ophthalmic use
SE9302201D0 (sv)	1993-06-24	1993-06-24	Leiras Oy	Composition for ophthalmic use
SE501482C2 (sv)	1993-06-24	1995-02-27	Leiras Oy	Komposition för topisk administration av bispilokarpinsyradiestrar till ögat i form av en vattenlösning
DE4334135A1 (de) *	1993-10-07	1995-04-13	Merck Patent Gmbh	Verfahren zur Herstellung von Pilocarpin-Derivaten

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4061722A (en)	1976-04-26	1977-12-06	Interx Research Corporation	Selected quaternary ammonium salts of pilocarpine useful in reducing intraocular pressure in warm-blooded animals
EP0106541A2 (de)	1982-09-17	1984-04-25	Hans Bundgaard	Vor-Arzneimittel von Pilocarpin

1990
- 1990-11-30 FI FI905930A patent/FI98815C/fi not_active IP Right Cessation
1991
- 1991-11-27 SK SK523-93A patent/SK52393A3/sk unknown
- 1991-11-27 AU AU89398/91A patent/AU664958B2/en not_active Ceased
- 1991-11-27 JP JP04500392A patent/JP3094232B2/ja not_active Expired - Fee Related
- 1991-11-27 HU HU9301569A patent/HUT67273A/hu unknown
- 1991-11-27 PL PL91308270A patent/PL168715B1/pl unknown
- 1991-11-27 AT AT91920512T patent/ATE192144T1/de not_active IP Right Cessation
- 1991-11-27 CA CA002096444A patent/CA2096444A1/en not_active Abandoned
- 1991-11-27 KR KR1019930701611A patent/KR930703264A/ko not_active Withdrawn
- 1991-11-27 DE DE69132143T patent/DE69132143T2/de not_active Expired - Fee Related
- 1991-11-27 CZ CS931025A patent/CZ282229B6/cs not_active IP Right Cessation
- 1991-11-27 RU RU93041054/04A patent/RU2100352C1/ru not_active IP Right Cessation
- 1991-11-27 PL PL91299375A patent/PL167773B1/pl unknown
- 1991-11-27 EP EP91920512A patent/EP0559700B1/de not_active Expired - Lifetime
- 1991-11-27 WO PCT/FI1991/000359 patent/WO1992009583A1/en not_active Ceased
- 1991-11-28 NZ NZ240781A patent/NZ240781A/xx unknown
1993
- 1993-05-28 LT LTIP577A patent/LT3532B/lt not_active IP Right Cessation
- 1993-05-28 LV LVP-93-436A patent/LV10094B/en unknown
- 1993-05-28 NO NO931960A patent/NO304228B1/no not_active IP Right Cessation
1994
- 1994-11-16 EE EE9400143A patent/EE9400143A/xx unknown

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4061722A (en)	1976-04-26	1977-12-06	Interx Research Corporation	Selected quaternary ammonium salts of pilocarpine useful in reducing intraocular pressure in warm-blooded animals
EP0106541A2 (de)	1982-09-17	1984-04-25	Hans Bundgaard	Vor-Arzneimittel von Pilocarpin

Also Published As

Publication number	Publication date
FI98815B (fi)	1997-05-15
EP0559700B1 (de)	2000-04-26
LV10094A (lv)	1994-05-10
PL167773B1 (pl)	1995-11-30
WO1992009583A1 (en)	1992-06-11
LTIP577A (en)	1994-12-27
NO931960D0 (no)	1993-05-28
EP0559700A1 (de)	1993-09-15
AU8939891A (en)	1992-06-25
CZ102593A3 (en)	1994-04-13
LV10094B (en)	1995-02-20
FI905930A7 (fi)	1992-05-31
HUT67273A (en)	1995-03-28
RU2100352C1 (ru)	1997-12-27
ATE192144T1 (de)	2000-05-15
JP3094232B2 (ja)	2000-10-03
JPH06504270A (ja)	1994-05-19
NO931960L (no)	1993-05-28
PL168715B1 (pl)	1996-03-29
EE9400143A (et)	1995-12-15
FI98815C (fi)	1997-08-25
KR930703264A (ko)	1993-11-29
NZ240781A (en)	1993-12-23
DE69132143D1 (de)	2000-05-31
AU664958B2 (en)	1995-12-07
DE69132143T2 (de)	2000-12-14
FI905930A0 (fi)	1990-11-30
CA2096444A1 (en)	1992-05-31
CZ282229B6 (cs)	1997-06-11
HU9301569D0 (en)	1993-09-28
NO304228B1 (no)	1998-11-16
SK52393A3 (en)	1994-01-12

Legal Events

Date	Code	Title	Description
1996-01-25	TK9A	Rectifications: patents	Free format text: 5. JUNGINIU, TURINCIU FORMULE I PAGAL 1 PUNKTA, GAVIMO BUDAS, B E S I S K I R I A N T I S TUO, KADA) SIEKIANT PAGAMINTI JUNGINI, KURIO FORMULE YRA I , (I ),KURIOJE A TURI REIKSMES, MINETAS 1 PUNKTE,PILOKARPINO RUGSTIS, KURIOS FORMULE YRAARBA JOS DRUSKA REAGUOJA SU JUNGINIU, KURIO FORMULE YRA X-A-X , KAI X IR X NEPRIKLAUSOMAI VIENAS NUO KITO YRA HIDROKSILAS, ARBA PALIEKANTI GRUPE, PAVYZDZIUI, HALOGENAS, ACILOKSIGRUPE, ARBA ALKIL- ARBA ARILSULFONILOKSIGRUPE, SIEKIANT PAGAMINTI JUNGINI, KURIO FORMULE YRA (II) (II),KURIS, JEI TO PAGEIDA
1997-11-25	PC9A	Transfer of patents	Free format text: SANTEN OY,NIITTYHAANKATU 20, FIN-33720 TAMPERE,FI,971017
2000-01-25	MM9A	Lapsed patents	Effective date: 19990528

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NO178968B (no)	1996-04-01	Analogifremgangsmåte for fremstilling av terapeutisk aktive aminopyrimidin-karboksamidderivater
PT90254B (pt)	1994-07-29	Processo para a preparacao de amidas de acidos ciclometileno -1,2-dicarboxilicos com actividade terapeutica e de composicoes farmaceuticas que as contem
US5436350A (en)	1995-07-25	Bispilocarpic acid ester derivatives and process for their preparation
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HK40058729A (en)	2022-04-29	Pharmaceutical composition comprising: 2-(((1r,4r)-4-(((4-chlorophenyl)(phenyl)carbamoyloxy)methyl)cyclohexyl)methoxy)acetic acid
KR810000762B1 (ko)	1981-07-02	신규크산틴유도체의 제조방법
KR850000274B1 (ko)	1985-03-15	나프트 이미다졸 및 나프트 옥사졸 유도체의 제조방법
JPH01261382A (ja)	1989-10-18	アルキレンジアミン誘導体
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